- 著者
- HIROSHI SUEMUNE TETSUJI HARABE ZHUO-FENG XIE KIYOSHI SAKAI
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.36, no.11, pp.4337-4344, 1988-11-25 (Released:2011-02-08)
- 参考文献数
- 14
- 被引用文献数
- 20 33
Asymmetric hydrolysis of 2, 2-bis (acetoxymethyl) cyclopentanone (5) using biocatalysts and its application to a formal synthesis of (-)-malyngolide are described.For the asymmetric induction at the quaternary carbon of 5, cholinesterase from electric eel was found to be effective to afford the (+)-monoacetate (6)(90%ee).Compound (+)-6 was easily converted to the synthetic intermediate (28) for (-)-malyngolide.
- 著者
- ZHUO-FENG XIE YUKINOBU ICHIKAWA HIROSHI SUEMUNE KIYOSHI SAKAI
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.35, no.5, pp.1812-1816, 1987-05-25 (Released:2009-10-19)
- 参考文献数
- 9
- 被引用文献数
- 4 7
The conversion of (+) -limonen-10-ol (7) into the key intermediate for the synthesis of carbacyclin (1), (+) - (1S, 2R, 3R, 5R) -3-acetoxy-2-methoxycarbony1-7-oxobicyclo [3.3.0] octane (2), is described. The cis-3, 4-disubstituted cyclopentanone prepared from 7 via a sequence of reactions involving Rh (I) -catalyzed cyclization could be converted to the 3-acetylbicyclo [3.3.0] oct-2-ene skeleton, which was subjected to 1, 4-addition reaction with CN-. The resulting cyano compound was transformed into the key intermediate 2 through appropriate modification of the substituents on the five-membered ring. This synthetic method provides a new route to carbacyclin.