Abstract: The present invention relates to a process of preparation of optically active antrocin. At first, to introduce the correct configuration of trans-decalone, alkyl aluminum/TMSCN was used to react with decalenone. The resulting racemic nitrile-decalone was resolved with chiral diol by ketalization to produce two chromatography separable diasteromers. After a simple column chromatography, optically pure compounds were obtained. Formylation was a critical step for the lactone formation. The rest of the synthesis is straight forward through oxidation and olefination. Accordingly, the total synthesis was completed in 10 steps with 7% overall yield from commercially available 6-methoxy-2-tetralone.
Type:
Grant
Filed:
September 14, 2012
Date of Patent:
February 25, 2014
Assignee:
Deyew Biotech Corp.
Inventors:
Dar-Fu Tai, Venkatachalam Angamuthu, Yew-Min Tzeng
Abstract: The present invention relates to a process of preparation of optically active antrocin. At first, to introduce the correct configuration of trans-decalone, alkyl aluminum/TMSCN was used to react with decalenone. The resulting racemic nitrile-decalone was resolved with chiral diol by ketalization to produce two chromatography separable diasteromers. After a simple column chromatography, optically pure compounds were obtained. Formylation was a critical step for the lactone formation. The rest of the synthesis is straight forward through oxidation and olefination. Accordingly, the total synthesis was completed in 10 steps with 7% overall yield from commercially available 6-methoxy-2-tetralone.
Type:
Application
Filed:
September 14, 2012
Publication date:
April 18, 2013
Applicant:
DEYEW BIOTECH CORP.
Inventors:
Dar-fu TAI, Venkatachalam ANGAMUTHU, Yew-min TZENG