An enantioselective route for the total synthesis of forskolin, a potent activator of adenylate cyclase, has been developed which is based on reduction of dienone 3 to the (S)-alcohol4 and conversion in two steps to tricyclic lactone 9, obtained in optically pure form simply by recrystallization. A
A total synthesis of (.+-.)-forskolin
β Scribed by Hashimoto, Shunichi.; Sakata, Shinji.; Sonegawa, Motoharu.; Ikegami, Shiro.
- Book ID
- 118010779
- Publisher
- American Chemical Society
- Year
- 1988
- Tongue
- English
- Weight
- 469 KB
- Volume
- 110
- Category
- Article
- ISSN
- 0002-7863
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π SIMILAR VOLUMES
A simple route for the enanrioselective synthesis of key intermediates (11 and 12) for the total synthesis of forskolin has been developed starting from acid 6 and (S)-alcohol 5. The latter is prepared by enantioselective catalytic CBS reduction of dienone 3, and is converted by an intramolecular Di
Preparation of the "Ziegler key intermediate" 2from lactone 3, readily obtained from hydroxy-O-ionone, was studied. In a first exploratory approach, lactones 11 and 13 were obtained but further transformations aimed at setting the ring junction were unsuccessful due to unexpected rearrangements. Thr