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Studies on the preparation of the “Ziegler intermediate”, a key intermediate in the total synthesis of forskolin

✍ Scribed by M. Leclaire; R. Levet; F. Péricaud; L. Ricard; J.Y. Lallemand

Publisher
Elsevier Science
Year
1996
Tongue
French
Weight
885 KB
Volume
52
Category
Article
ISSN
0040-4020

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✦ Synopsis

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. Through a straightforward synthetic sequence involving two new rearrangements, lactone 3 was converted to diosphenol 21 with the desired trans A/B ring junction. 21 was in turn transformed into the well-known acetonide 2 in a good yield. This constitutes a new formal total synthesis offorskolin.

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