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A short and efficient enantioselective route to a key intermediate for the total synthesis of forskolin

✍ Scribed by E.J Corey; Paul Da Silva Jardine


Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
285 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis


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 Diels-Alder reaction to tricyclic lacrone 9.


πŸ“œ SIMILAR VOLUMES


Enantioselective route to a key intermed
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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

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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