Abstract: Bicycloalkane derivatives of the formula ##STR1## WHEREIN N IS 1 OR 2, R.sub.1 is lower alkyl, X is carbonyl or free or etherified hydroxymethylene, and Y is --S--R.sub.2, --SO.sub.m --R.sub.2, or ##STR2## wherein m is 1 or 2, R.sub.2 is alkyl, R.sub.3 is hydrogen or lower alkyl, R.sub.4 is aliphatic acyl and Z is nitro, lower alkanoyl, lower alkylsulfinyl, or lower alkylsulfonyl are useful intermediates in the total synthesis of steroids. The compounds are prepared by reacting a corresponding compound lacking the CH.sub.2 Y substituent with formaldehyde and a mercaptan or a sulfinic acid, followed if desired by oxidation and optional salt condensation.

Abstract: Novel 1,3-dialkoxy 8.alpha.-estratriene compounds of the formula ##STR1## WHEREIN R.sub.1 is alkyl of 1-18 carbon atoms, R.sub.2 is alkyl of 1-5 carbon atoms and Ac is alkanoyl of 1-8 carbon atoms, are obtained by a three-step synthesis from a tetrahydroindane-5-one compound.

Abstract: D-homosteroids of the formula ##STR1## WHEREIN R.sup.3.alpha. is hydrogen, R.sup.3.beta. is hydroxy, lower alkanoyloxy or aroyloxy and R.sup.3.alpha. and R.sup.3.beta. taken together are oxo; R.sup.17a.alpha. is hydrogen, lower alkyl, ethynyl, vinyl, allyl, methallyl, propadienyl, 1-propynyl, butadiynyl or chloroethynyl; R.sup.17a.beta. is hydrogen, alkanoyl, aroyl, lower alkyl, cycloalkyl-lower-alkyl, benzyl, furfuryl or tetrahydropyranyl; R.sup.18 is hydrogen or methyl and the dotted line in the C-ring denotes an additional carbon to carbon bond in the 11,12-position andProcesses for the preparation thereof are disclosed.The D-homosteroids of the present invention are useful as ovulation inhibitors and androgenic/anabolic agents.

Abstract: Bicycloalkane derivatives of the formula ##STR1## WHEREIN N IS 1 OR 2, R.sub.1 is lower alkyl, X is carbonyl or a free or etherified hydroxymethylene, and Y is --S--R.sub.2, --SO.sub.m --R.sub.2, or ##STR2## wherein m is 1 or 2, R.sub.2 is aryl or aralkyl, R.sub.3 is hydrogen or lower alkyl, R.sub.4 is phenyl optionally substituted with lower alkoxy or benzyloxy, and Z is nitro, lower alkanoyl, lower alkylsulfinyl, or lower alkylsulfonyl, are useful intermediates in the total synthesis of steroids. The compounds are prepared by reacting a corresponding compound lacking the CH.sub.2 Y substituent with formaldehyde and a mercaptan or a sulfinic acid, followed if desired by oxidation and optional salt condensation.

Abstract: Benzopyran derivatives of the formula ##STR1## wherein R.sub.1 and R.sub.3 each are lower alkyl; n is the integer 1 or 2; --A--B-- is >CH--CH.sub.2 - or >CH=CH-; X is a free, esterified or etherified hydroxy group; and Y is H or X and Y collectively are =O; and W is --(CH.sub.2).sub.3 --Z--R.sub.4 ##STR2## --(CH.sub.2).sub.3 --COOR.sub.6 or --(CH.sub.2).sub.3 CN, wherein V is halogen, Z is a ketalized carbonyl group or a free, esterified or etherified hydroxymethylene group; R.sub.4 and R.sub.5 each are lower alkyl and R.sub.6 is alkyl, aryl or aralkyl, are valuable intermediates in the synthesis of steroids.

Abstract: Novel process for the preparation of 13.beta.-alkyl-4-gonene-3,17-diones of the formula ##STR1## wherein R.sub.1 is methyl or ethyl, consists of REACTING A 7A.beta.

Abstract: Bicycloalkanes useful as intermediates in the total synthesis of steroids of the formula ##STR1## WHEREIN N IS THE INTEGER 1 OR 2; R.sub.1 is lower-alkyl; X is free or ketalized carbonyl or free, esterified or etherified hydroxymethylene; and Y is --SO.sub.2 --R.sub.2 or --C(Z)(R.sub.3)--R.sub.4 wherein R.sub.2 is alkyl, aryl or aralkyl R.sub.3 is H or lower-alkyl, R.sub.4 is alkoxycarbonyl or acyl and Z is lower-alkoxycarbonyl, lower acyl, lower alkylsulfinyl or lower-alkylsulfonyl, are produced by the steps of hydrogenating a compound of the formula ##STR2## AND CONDENSING THE THUS-PRODUCED RING SATURATED COMPOUND WITH A SALT OF THE FORMULA C(Z)(R.sub.3)R.sub.4 .sup.-Me.sup.+ wherein n, X, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and Z have the values given above.

Abstract: 9,10-Secoestranes, useful as intermediates in the total synthesis of steroids, of the formula ##STR1## WHEREIN N IS 1 OR 2, R.sub.1 is lower alkyl, R.sub.2, R.sub.3 and R.sub.4 are hydrogen, alkoxy or acyloxy, X is free or ketalized carbonyl or free, esterified or etherified hydroxymethylene, and Y is carbonyl or dialkoxymethylene are produced by condensing, in the presence of a basic catalyst, ##STR2## WHEREIN X, n, R.sub.1, R.sub.2, R.sub.3, R.sub.4 have the values given above, and Z is Cl, Br or I, to produce a 9,10-secoestrane of the above formula wherein Y is a free carbonyl group, which can then, if desired, be ketalized to a corresponding compound wherein Y is dialkoxymethylene or like ketal group.

Abstract: Bicycloalkane derivatives of the formula ##STR1## WHEREIN N IS 1 OR 2, R.sub.1 is lower alkyl, X is free or ketalized carbonyl or a free, esterified, or etherified hydroxymethylene, and Y is --S--R.sub.2, --SO.sub.m --R.sub.2, or ##STR2## wherein m is 1 or 2, R.sub.2 is alkyl, aryl, or aralkyl, R.sub.3 is hydrogen or lower alkyl, R.sub.4 is alkoxycarbonyl, or acyl or phenyl optionally substituted with lower alkoxy or benzyloxy- or acyloxy; and Z is nitrile, nitro, lower alkoxycarbonyl, lower alkanoyl, lower alkylsulfinyl, or lower alkylsulfonyl are useful intermediates in the total synthesis of steroids. The compounds are prepared by reacting a corresponding compound lacking the CH.sub.2 Y substituent with formaldehyde and a mercaptan or a sulfinic acid, followed if desired by oxidation and optional salt condensation.

Abstract: 9,10-Secoestranes, useful as intermediates in the total synthesis of steroids, of the formula ##STR1## WHEREIN N IS 1 OR 2, R.sub.1 is lower alkyl, R.sub.2, R.sub.3 and R.sub.4 are hydrogen, alkoxy or acyloxy, X is free or ketalized carbonyl or free, esterified or etherified hydroxymethylene, and Y is carbonyl or dialkoxymethylene are produced by condensing, in the presence of a basic catalyst, ##STR2## WHEREIN X, n, R.sub.1, R.sub.2, R.sub.3, R.sub.4 have the values given above, and Z is Cl, Br or I, to produce a 9,10-secoestrane of the above formula wherein Y is a free carbonyl group, which can then, if desired, be ketalized to a corresponding compound wherein Y is dialkoxymethylene or like ketal group.

Abstract: 9,10-Secoestranes, useful as intermediates in the total synthesis of steroids, of the formula ##STR1## wherein n is 1 or 2, R.sub.1 is lower alkyl, R.sub.2, R.sub.3 and R.sub.4 are hydrogen, alkoxy or acyloxy, X is free or ketalized carbonyl or free, esterified or etherified hydroxymethylene, and Y is carbonyl or dialkoxymethylene are produced by condensing, in the presence of a basic catalyst, ##STR2## WHEREIN X, n, R.sub.1, R.sub.2, R.sub.3, R.sub.4 have the values given above, and Z is Cl, Br or I, to produce a 9,10-secoestrane of the above formula wherein Y is a free carbonyl group, which can then, if desired, be ketalized to a corresponding compound wherein Y is dialkoxymethylene or like ketal group.

Abstract: 6,9-Oxido-9,10-seco-1,3,5(10),6,8,14-estrahexaenes, useful as intermediates in the total synthesis of steroids, of the formula ##SPC1##Wherein n is 1 or 2, R.sub.1 is lower-alkyl, R.sub.2, R.sub. 3 and R.sub.4 are H, alkoxy or acyloxy, X is a free or ketalized keto or free, esterified or etherified hydroxymethylene, are produced by the cyclization, with an acid catalyst, of a 9,10-secoestrane of the formula ##SPC2##Wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, X and n have the values given above, and Q is carbonyl or dialkoxymethylene. Hydrogenation produces the corresponding 6,9-oxido-9,10-seco-1,3,5(10)-estratrienes and 9-oxy-9,10-seco-1,3,5(10)-estratrienes.

Abstract: 6,9-Oxido-9,10-seco-1,3,5(10),6,8,14-estrahexaenes, useful as intermediates in the total synthesis of steroids, of the formula ##SPC1##Wherein n is 1 or 2, R.sub.1 is lower-alkyl, R.sub.2, R.sub.3 and R.sub.4 are H, alkoxy or acyloxy, X is a free or ketalized keto or free, esterified or etherified hydroxymethylene, are produced by the cyclization, with an acid catalyst, of a 9,10-secoestrane of the formula ##SPC2##Wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, X and n have the values given above and Q is carbonyl or dialkoxymethylene. Hydrogenation produces the corresponding 6,9-oxido-9,10-seco-1,3,5(10)-estratrienes and 9-oxy-9,10-seco-1,3,5(10)-estratrienes.

Abstract: Novel benzopyran derivatives of the formula ##SPC1##Wherein R.sub.1 and R.sub.3 each are lower alkyl; n is the integer 1 or 2; --A--B-- is >CH--CH.sub.2 -- or >CH=CH--; X is a free, esterified or etherified hydroxy group; and Y is H or X and Y collectively are =O; and W is --(CH.sub.2).sub.3 --Z--R.sub.4,--(ch.sub.2).sub.3 --coor.sub.6 or --(CH.sub.2).sub.3 CN, wherein V is halogen, Z is a ketalized carbonyl group R.sub.4 and R.sub.5 each are lower alkyl and R.sub.6 is alkyl, aryl or aralkyl, are valuable intermediates in the synthesis of steroids.

Abstract: 20-Cyano-17.alpha.-H steroids having as the 17-position substituent the group ##EQU1## wherein R is H, alkyl of 1-8 carbon atoms or benzyl, having a 13-methyl or 13-ethyl group and which are unsubstituted or substituted with an .alpha.-methyl group in the 16-position are converted to the corresponding 20-keto steroids by reaction in an aprotic solvent with a deprotonating agent containing an alkali metal, an alkaline earth metal, copper(I) or thallium(I), and optionally additionally with a copper(I) salt or a thallium(I) salt or a silver(I) salt, and thereafter conducting an oxidative splitting reaction with oxygen. The thus-produced 17.beta.-oxalyl steroids possess pharmacological activity, e.g., anti-inflammatory activity, or are useful as intermediates for the production of pharmacologically active steroids.