The Bicyclo Ring System Consists Of Two Five-membered Rings Patents (Class 549/311)
  • Patent number: 9823563
    Abstract: To provide an alcohol compound containing fewer impurities at a high yield by conducting the following steps: a hydroboration process in which a reaction mixture is obtained by reacting in a solvent a compound represented by formula (C) and a boron agent selected from a group of diborane and borane complexes; and an oxidation process in which the pH of the reaction mixture is set at 0.5 to 4, which is conducted after treating the reaction mixture with hydrogen peroxide. In the formula, A1 to A6 are each independently a hydrogen atom, methyl group or ethyl group, and X is an oxygen atom, sulfur atom, methylene group or ethylene group.
    Type: Grant
    Filed: June 14, 2012
    Date of Patent: November 21, 2017
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Satoshi Sakuma, Masashi Serizawa, Atsushi Yasuda, Nobuhisa Yada, Shinichi Maeda
  • Publication number: 20130217898
    Abstract: The present invention relates to a method for manufacturing an ester from a ketone or an aldehyde, which is a reactive substrate, by a Baeyer-Villiger oxidation reaction using hydrogen peroxide, and in this method, as a catalyst, M(BAr4)n, which is a metal borate, is used (M represents an alkali metal or an alkaline earth metal; Ar represents an aryl; and n is the same number as the valence of M). For example, when cyclohexanone was used as the reactive substrate, and Sr[B(3,5-CF3C6H3)4]2 was used as the catalyst, ?-caprolactone was obtained at an isolated yield of 82%.
    Type: Application
    Filed: October 11, 2011
    Publication date: August 22, 2013
    Applicant: NATIONAL UNIVERSITY CORPORATION NAGOYA UNIVERSITY
    Inventors: Kazuaki Ishihara, Muhammet Uyanik
  • Publication number: 20130197077
    Abstract: A class of bicyclic brominated furanone structures that have reduced toxicity and high activity for inhibiting biofilm formation and quorum sensing by microbes. The molecules have two fused cyclic alkyl groups that provide a structural framework that retain one or more bromine groups on the structure. The bicyclic furanones have reduced toxicity to mammalian cells as compared to other brominated furanones but retain the ability to inhibit biofilm formation in bacterial populations.
    Type: Application
    Filed: January 25, 2013
    Publication date: August 1, 2013
    Applicant: SYRACUSE UNIVERSITY
    Inventor: Syracuse University
  • Publication number: 20120209011
    Abstract: This invention relates to novel process for the preparation of prostaglandin compounds having formula (K), wherein R is selected from the group consisting of C1-C7 alkyl; C7-C17 aralkyl wherein the aryl group is unsubstituted or substituted with one to three substituents selected from the group consisting of C1-C6 alkyl, halo and CF3; and (CH2)nOR2 wherein n is from 1 to 3 and R2 represents a C6-C10 aryl group which is unsubstituted or substituted with one to three substituents selected from the group consisting of C1-C6 alkyl, halo and CF3; and R1 is selected from OR3 and NHR3 wherein R3 is C1-C6 alkyl, H; and dashed lines represents a double bond or a single bond, is disclosed. Novel intermediates are also disclosed.
    Type: Application
    Filed: December 21, 2009
    Publication date: August 16, 2012
    Inventors: Chandrashekar Aswathanarayanappa, Pullela Venkata Srinivas, Divya Kangath, Thilak Gregory Soundararajan, Anegondi Sreenivasa Prasad, Suriyan Masinaickenpatty Raghavendran
  • Publication number: 20120088160
    Abstract: The present technology relates to stabilizing additives and electrolytes containing the same for use in electrochemical devices such as lithium ion batteries and capacitors. The stabilizing additives include triazinane triones and bicyclic compounds comprising succinic anhydride, such as compounds of Formulas I and II described herein.
    Type: Application
    Filed: October 7, 2010
    Publication date: April 12, 2012
    Inventors: Lu Zhang, Zhengcheng Zhang, Khalil Amine
  • Publication number: 20120058430
    Abstract: A positive resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under the action of acid and an acid-generator component (B) which generates acid upon exposure, wherein the acid-generator component (B) includes an acid generator (B1) containing a compound represented by general formula (b1-1) shown below (wherein Z+ represents an organic cation).
    Type: Application
    Filed: September 1, 2011
    Publication date: March 8, 2012
    Applicant: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoshiyuki Utsumi, Takehiro Seshimo
  • Publication number: 20110201809
    Abstract: A process of making entecavir comprising converting a compound of formula (M5) to entecavir, wherein the two PGs on the formula (M5) are taken together to form an optionally substituted six- or seven-member cyclic ring.
    Type: Application
    Filed: February 15, 2011
    Publication date: August 18, 2011
    Inventors: Tsung-Cheng Hu, Hung-Tsung Huang
  • Publication number: 20110092368
    Abstract: The present invention relates to novel 2,4,6-phenyl-substituted cyclic ketoenols of the formula (I) in which W, X, Y and CKE have the meanings given in the disclosure, to a plurality of processes for their preparation and to their use as pesticides and/or herbicides. The invention further relates to selectively herbicidal compositions containing 2,4,6-phenyl-substituted cyclic ketoenols and a compound which improves crop plant tolerance.
    Type: Application
    Filed: December 17, 2010
    Publication date: April 21, 2011
    Inventors: Reiner Fischer, Klaus Kunz, Stefan Lehr, Michael Ruther, Udo Schneider, Markus Dollinger, Mark Wilhelm Drewes, Dieter Feucht, Jörg Konze, Ulrike Wachendorff-Neumann, Guido Bojack, Thomas Auler, Martin Jeffrey Hills, Thomas Bretschneider, Olga Malsam, Christoph Erdelen, Angelika Lubos-Erdelen, Alfred Angermann, Hein Kehne, Christopher Hugh Rosinger
  • Publication number: 20100041889
    Abstract: The present invention relates to synthesis procedures and intermediates of a compound of formula: and the salts thereof.
    Type: Application
    Filed: February 1, 2008
    Publication date: February 18, 2010
    Inventors: Andras Horvath, Dominique Paul Michel Depré, Dominic John Ormerod
  • Patent number: 7595408
    Abstract: The present invention relates to methods for the preparation of diastereomerically pure (3R,3aS,6aR) hexahydro-furo[2,3-b]furan-3-ol as well as a novel intermediate, (3aR,4S,6aS) 4-methoxy-tetrahydro-furo[3,4-b]furan-2-one for use in said methods. More in particular the invention relates to a stereoselective method for the preparation of diastereomerically pure (3R,3aS,6aR) hexahydro-furo[2,3-b]furan-3-ol, as well as methods for the crystallization of (3aR,4S,6aS) 4-methoxy-tetrahydro-furo[3,4-b]furan-2-one and for the epimerization of (3aR,4R,6aS) 4-methoxy-tetrahydro-furo[3,4-b]-furan-2-one to (3aR,4S,6aS) 4-methoxy-tetrahydro-furo[3,4-b]furan-2-one.
    Type: Grant
    Filed: March 31, 2005
    Date of Patent: September 29, 2009
    Assignee: Tibotec Pharmaceuticals, Ltd.
    Inventors: Peter Jan Leonard Mario Quaedflieg, Bart Rudolf Romanie Kesteleyn, Robert Jan Vijn, Constantinus Simon Maria Liebregts, Jacob Hermanus Matheus Hero Kooistra, Franciscus Alphons Marie Lommen
  • Patent number: 7276089
    Abstract: Compositions for the oxidative dyeing of keratin fibers, comprising a medium suitable for dyeing and at least one bicyclic fused 5-5-membered aza heteroaromatic keratin dyeing compound with an N-hydroxy or N-amino group and derivatives thereof. A method for oxidative dyeing of keratin fibers, comprising applying such compositions in the presence of an oxidizing agent, for a period sufficient to develop the desired coloration.
    Type: Grant
    Filed: August 23, 2005
    Date of Patent: October 2, 2007
    Assignee: The Procter & Gamble Company
    Inventors: Robert Wayne Glenn, Jr., Mu'Ill Lim
  • Patent number: 6784302
    Abstract: An optically active lactone compound is produced by using a Zr(salen) complex of the following formula (I) or its enantiomer as a catalyst and subjecting a cyclic ketone compound to a Baeyer-Villiger reaction with at least one oxidizer selected from hydrogen peroxide, aqueous hydrogen peroxide and urea-hydrogen peroxide adduct in a solvent: wherein Ar1 is an aryl group having a carbon number of 10 to 16 and Y is a phenoxy group or an alkoxy group having a carbon number of 1 to 10.
    Type: Grant
    Filed: April 3, 2003
    Date of Patent: August 31, 2004
    Assignee: Kyushu University
    Inventors: Tsutomu Katsuki, Akira Watanabe, Tatsuya Uchida
  • Patent number: 6462074
    Abstract: The present invention relates to novel substituted (&agr;,&bgr;-fused butyrolactones, to processes for their preparation and to their use for the prevention and/or treatment of disorders caused by hyper- or hypofunction of the glutamatergic system, in particular of cerebral ischaemias, craniocerebral trauma, states of pain or CNS-mediated spasms.
    Type: Grant
    Filed: July 14, 2000
    Date of Patent: October 8, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Andreas Stolle, Horst-Peter Antonicek, Stephen Lensky, Arnd Voerste, Thomas Müller, Jörg Baumgarten, Karsten von dem Bruch, Gerhard Müller, Udo Stropp, Ervin Horváth, Jean-Marie-Viktor de Vry, Rudy Schreiber
  • Patent number: 6268514
    Abstract: The use of nitroethane derivatives of the formula I where: R1 is hydrogen, unsubstituted or substituted C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, halogen, cyano or thiocyanato; R2 is hydrogen, formyl; halogen- or C1-C3-alkoxy-substituted or unsubstituted C1-C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C4-C6-alkyldienylcarbonyl or C2-C6-alkynylcarbonyl; A is unsubstituted or substituted phenyl, naphthyl, quinolyl, quinazolyl, quinoxalyl, 1-methylindolyl, 1-methylbenzimidazolyl, 2-methylindazolyl, benzofuranyl, benzothienyl, benzoxazolyl, benzothiazolyl, furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl or triazinyl, pyranyl or thiopyranyl; as microbicides is described.
    Type: Grant
    Filed: June 13, 2000
    Date of Patent: July 31, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Hamprecht, John-Bryan Speakman, Gisela Lorenz, Kurt Eger, Mathias Schmidt, Uta Witt
  • Patent number: 5912361
    Abstract: Trehalose is oxidized to give oxidized trehalose which then is hydrolyzed to produce D-glucuronolactone which is thereafter recovered to realize high-yield and low-cost production of D-glucuronolactone.
    Type: Grant
    Filed: March 9, 1998
    Date of Patent: June 15, 1999
    Assignees: Chugoku Kayaku Kabushiki Kaisha, Hayashibara Biochemical Laboratories, Inc.
    Inventors: Toshiki Tsuchioka, Tadashi Yamaguchi, Kunihiko Yuuen, Hiroto Chaen
  • Patent number: 5840923
    Abstract: An optically-purified enantiomer of the lactone 4-hydroxy-2-oxabicyclo-?3.3.0!oct-7-en-3-one or an acylate thereof can be obtained by biotransformation. It is a useful synthon in the preparation of an enantiomer of 3-hydroxymethyl-2-hydroxycyclopentene that can be used to prepare carbocyclic nucleosides as a desired enantiomer.
    Type: Grant
    Filed: October 21, 1994
    Date of Patent: November 24, 1998
    Assignee: Chiroscience Limited
    Inventors: Stanley Michael Roberts, Horacio F. Olivo, Raymond McCague
  • Patent number: 5717098
    Abstract: A process for the preparation of a .gamma.-lactone of the formula ##STR1## which can be used to produce a single enantiomer of aminoazanoradamantane which is coupled to aromatic acid moieties to produce compounds useful as 5-HT agonists or antagonists.
    Type: Grant
    Filed: July 22, 1996
    Date of Patent: February 10, 1998
    Assignee: G. D. Searle & Co.
    Inventors: Daniel Paul Becker, Daniel Lee Flynn, Alan Edward Moormann, Clara Ines Villamil
  • Patent number: 5541344
    Abstract: The present invention is directed to intermediates of the formula ##STR1## which are useful in a process for the preparation of aminoazanoradamanatanes.
    Type: Grant
    Filed: May 19, 1995
    Date of Patent: July 30, 1996
    Assignee: G. D. Searle & Co.
    Inventors: Daniel P. Becker, Daniel L. Flynn, Alan E. Moormann, Clara I. Villamil
  • Patent number: 5538995
    Abstract: A difluoroprostacyclin of the following formula (V), its lower alkanol ester or its pharmaceutically acceptable salt: ##STR1## wherein A is an ethylene group, a vinylene group or an ethynylene group, R is a substituted or unsubstituted C.sub.1-10 alkyl group, a substituted or unsubstituted C.sub.1-10 alkenyl group, a substituted or unsubstituted C.sub.1-10 alkynyl group, a substituted or unsubstituted C.sub.3-8 cycloalkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryloxy group, Q is a substituted or unsubstituted C.sub.1-10 alkyl group, a substituted or unsubstituted C.sub.1-10 alkenyl group, a substituted or unsubstituted C.sub.1-10 alkynyl group, a substituted or unsubstituted C.sub.3-8 cycloalkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group.
    Type: Grant
    Filed: February 17, 1995
    Date of Patent: July 23, 1996
    Assignee: Asahi Glass Company Ltd.
    Inventors: Yasushi Matsumura, Takashi Nakano, Mayumi Makino, Yoshitomi Morizawa
  • Patent number: 5442079
    Abstract: There are described improved processes for the synthesis of a desired lactone useful as a synthon, the improved processes comprising oxidizing a protected arene diol with permanganate and periodate or subjecting a substituted epoxydiol to periodate oxidation to yield the desired lactone.
    Type: Grant
    Filed: May 10, 1993
    Date of Patent: August 15, 1995
    Assignee: Virginia Polytechnic Institute and State University
    Inventors: Tomas Hudlicky, Martin Mandel
  • Patent number: 5374745
    Abstract: The invention relates to a process for the production of prostaglandin precursors of formula I ##STR1## as well as their enantiomers in which X is A--W or W--A,A is a --C.tbd.C-- group,W is a hydroxymethylene group, in which the OH group can be functionally modified by etherification or esterification,D is a straight-chain or branched-chain alkylene group with 2-5 C atoms each or a ##STR2## group, n i s 1 to 3,E is a --C.tbd.C-- group or a --CR.sub.3 .dbd.CR.sub.4 group with R.sub.3 and R.sub.4 each meaning a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group,R.sub.1 is a hydrogen atom or a hydroxy group, which can be functionally modified as in W,R.sub.2 is a straight-chain or branched-chain alkyl group with 1-7 C atoms, characterized in that vinyl bromides of formula II ##STR3## in which Z means the group ##STR4## and R.sub.1, W, D, E and R.sub.2 have the above-indicated meanings and hydroxy groups unprotected in R.sub.1 and W or represented by an optionally substituted benzoyl radical, a C.sub.1 -C.sub.
    Type: Grant
    Filed: September 29, 1992
    Date of Patent: December 20, 1994
    Assignee: Schering Aktiengesellschaft
    Inventor: Ulrich Klar
  • Patent number: 5274097
    Abstract: Novel 1,3-disubstituted pyrrolidines active on the central nervous system of the formula ##STR1## wherein A--denotes phenyl or hetaryl, which is optionally fused with aromatic, saturated or unsaturated cyclic or heterocyclic hydrocarbons, where this radical can optionally be substituted,X--denotes --O--CH.sub.2 --, --CH.sub.2 --O-- or --O--,n--denotes a number from 1 to 19, andB--denotes cyano or a group of the formula --COOR.sup.1, --CONR.sup.2 R.sup.3, --SO.sub.2 NR.sup.2 R.sup.3, --SO.sub.m R.sup.4, --NR.sup.5 R.sup.6, or --C.tbd.C--CH.sub.2 --NR.sup.5 R.sup.6,and salts thereof.
    Type: Grant
    Filed: April 9, 1991
    Date of Patent: December 28, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rudolf Schohe, Peter-Rudolf Seidel, Jorg Traber, Thomas Glaser
  • Patent number: 5219743
    Abstract: The primary hydroxy group of Corey lactone diols is optically selectively acylated to obtain the desired optically active ester and/or diol. The mixture of Corey lactone diols of formulae (Ia) and (Ib): ##STR1## is reacted with an acylating agent optically selectively in the presence of an enzyme and/or a microorganism thereby to acylate, isolate and purify the primary alcohol.
    Type: Grant
    Filed: February 18, 1992
    Date of Patent: June 15, 1993
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Seiichi Takano, Tsutomu Sugahara
  • Patent number: 4973713
    Abstract: A process for the production of esters or lactones, comprising reacting in the presence of a catalyst and under hydrogenation conditions hydrogen and an acyclic or cyclic carboxylic anhydride to produce the corresponding ester or lactone, wherein the catalyst is a supported catalyst comprising:(a) a group VIII metal, Re and Fe;(b) a group VIII metal on TiO.sub.2 ;(c) Ru and at least one of Re, Ag or Cu; or(d) Pd and Fe.Preferably, the anhydride has the formula ##STR1## and is reacted to form an ester of the formula ##STR2## or a lactone of the formula ##STR3## wherein R and R.sup.1 independently are lower alkyl or cycloalkyl; R.sup.2, R.sup.3, R.sup.4, R.sup.5 independently are hydrogen, lower alkyl, cycloalkyl or aryl; and wherein R.sup.3 and R.sup.4 taken together may form a saturated or unsaturated ring, or an aromatic ring. The more preferred starting material is phthalic anhydride.
    Type: Grant
    Filed: November 28, 1989
    Date of Patent: November 27, 1990
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: William H. Manogue
  • Patent number: 4808734
    Abstract: 16-Cycloalkyl-7-fluoro prostacyclins having a 16 lower alkyl or fluoro substituent useful as blood platelet anti-aggregating agent, vasodilators, cyto protective lowering agents, anti-ulcerogenic agent and for treating peripheral vascular diseases such as schleroderma.
    Type: Grant
    Filed: December 1, 1986
    Date of Patent: February 28, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: George W. Holland, Perry Rosen, Hans Maag, Ferdinand Lee
  • Patent number: 4772728
    Abstract: A method for making a bicyclic lactone comprising heating under aqueous acidic conditions a beta, gamma unsaturated cyclic nitrile and an aldehyde, for a length of time sufficient to convert at least a portion of the reactants to a bicyclic lactone of the formula ##STR1## wherein R.sub.3 is --H; R.sub.4, R.sub.5, and R.sub.6 are independently selected from the group consisting of --H, --CH.sub.3 ; R.sub.2 is selected from the group consisting of --H, --CH.sub.3, and --CH.sub.3, and --C.sub.2 H.sub.5 ; R.sub.8 is --H or --CH.sub.3 ; m is an integer from 1 to 5; o is 0, 1, 2, or 3; and p is 0, 1, or 2; provided that the sum of m+o+p is an integer from 3 to 5; either R.sub.3 or R.sub.8 together with R.sub.7 represents a carbon-carbon bond. The method uses commercially available and relatively inexpensive raw materials as reactants.
    Type: Grant
    Filed: August 19, 1985
    Date of Patent: September 20, 1988
    Assignee: Angus Chemical Company
    Inventors: Stephan Korte, Craig W. Coulston, Friedhelm Korte
  • Patent number: 4707555
    Abstract: New optically active intermediates and processes thereto are provided for use in synthesizing therapeutically active prostaglandins of the formula: ##STR1## wherein R.sup.1 is hydrogen or lower alkyl; from a compound of the formula: ##STR2## wherein R.sup.1 is as above and R.sup.2 is hydrogen or a carboxy blocking group convertible to an acid by hydrolysis.
    Type: Grant
    Filed: July 12, 1985
    Date of Patent: November 17, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventors: David L. Coffen, George W. Holland, W. Harry Mandeville, Perry Rosen, Frederick Wong
  • Patent number: 4672132
    Abstract: A process for producing 3-oxo-6-formyl-2-oxabicyclo[3.3.0]-6-octene useful as an intermediate for producing prostaglandins, via a few steps from raw materials which can be relatively easily prepared. The process comprises subjecting 2,2-dimethyl-1,3-dioxin-4-one and cis-2-cyclopenten-1,4-diol to addition reaction in a solvent, preferably under a photo-irradiation, removing the solvent from the reaction mixture, adding water to the resulting adducts and reacting the resulting mixture on heating.
    Type: Grant
    Filed: February 28, 1986
    Date of Patent: June 9, 1987
    Assignee: Chisso Corporation
    Inventors: Chikara Kaneko, Masayuki Sato
  • Patent number: 4661286
    Abstract: This invention is directed to oxaspirododecane derivatives, the preparation thereof, and perfume compositions containing same.
    Type: Grant
    Filed: March 24, 1986
    Date of Patent: April 28, 1987
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Ulf A. Schaper, Siegfried Bloesl, Klaus Bruns
  • Patent number: 4558140
    Abstract: New optically active intermediates and processes thereto are provided for use in synthesizing therapeutically active prostaglandins of the formula: ##STR1## wherein R.sup.1 is hydrogen or lower alkyl; from a compound of the formula: ##STR2## wherein R.sup.1 is as above and R.sup.2 is hydrogen or a carboxy blocking group convertible to an acid by hydrolysis.
    Type: Grant
    Filed: March 6, 1984
    Date of Patent: December 10, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: David L. Coffen, George W. Holland, Perry Rosen, Frederick Wong
  • Patent number: 4485246
    Abstract: The rate of selective hydrogenation of carboxylic acid anhydrides to esters or lactones in the presence of a ruthenium organophosphorous catalyst which contains or liberates a hydrogen halide during the hydrogenation, is improved by providing in the reaction medium prior to or during the hydrogenation a basic amino compound to remove the hydrogen halide.
    Type: Grant
    Filed: October 29, 1982
    Date of Patent: November 27, 1984
    Assignee: Sun Tech, Inc.
    Inventor: James E. Lyons
  • Patent number: 4485245
    Abstract: Process for selective homogeneous catalytic hydrogenation of carboxylic acid anhydrides to ester or lactones at an improved rate and to obtain improved yields wherein the catalyst is a ruthenium trichlorostannate complex of the formula: ##STR1## wherein X is hydrogen, chlorine, bromine, iodine or lower alkyl; m is the integer 1 or 2; n is an integer of from 0 to 3 but when n is 2 or 3, X may be the same or different; M is P, As or Sb; R.sup.6, R.sup.7 and R.sup.8 independently are lower alkyl, cycloalkyl, aryl, benzyl or a bidentate legand; x is an integer of from 1 to 4 but when x is 2 or more, M may be the same or different; L is a neutral ligand, olefin, CO or (R.sup.9).sub.2 CO wherein R.sup.9 is lower alkyl; y is an integer of from 0 to 3 but when y is 2 or 3, L may be the same or different; and the sum of x and y is at least 2.
    Type: Grant
    Filed: October 29, 1982
    Date of Patent: November 27, 1984
    Assignee: Sun Tech, Inc.
    Inventors: Chao-Yang Hsu, James E. Lyons
  • Patent number: 4463183
    Abstract: A method is provided for preparing compounds of the formulae ##STR1## wherein A may be --C.dbd.C-- or --C.tbd.C--, by reducing an epoxy lactone of the structure ##STR2## to form the corresponding epoxy hemiacetal, reacting the epoxy hemiacetal with a silyl compound to form an epoxy silyl acetal, reacting the epoxy silyl acetal with an acetylenic derivative to form a silyl acetal, removing the silyl protecting group to form a hemiacetal, reacting the hemiacetal compound with an appropriate Wittig reagent to form a protected difluoro PGF.sub.2.alpha. type compound, removing the protecting group, reacting the difluoro PGF.sub.2.alpha. with an iodine compound to form an iodoether and reacting the iodoether with a base to form the desired compounds.Novel intermediates produced in the above method are also provided.
    Type: Grant
    Filed: April 25, 1983
    Date of Patent: July 31, 1984
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Martin F. Haslanger