Journal of Organic Chemistry p. 4714 - 4718 (1991)
Update date:2022-08-04
Topics: Isomerization Final steps
Chadha, N. K.
Batcho, A. D.
Tang, P. C.
Courtney, L. F.
Cook, C. M.
et al.
An asymmetric synthesis of tetrahydrolipstati (4) is described.Application of our previously described in situ cyclopentadiene alkylation-asymmetric hydroboration protocol provided the key chiral alcohol 9.In the course of this work, the presence of a free hydroxyl group was found to exert a strong directing effect on the regioselectivity of a Baeyer-Villiger reaction (16 --> 17).Subsequent transformations of lactone 17 produced tetrahydrolipstatin.
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