Catalytic Asymmetric Synthesis of Both syn- and anti-3,5-Dihydroxy Esters: Application to 1,3-Polyol/α-Pyrone Natural Product Synthesis
- 29 January 2003
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (4) , 495-498
- https://doi.org/10.1021/ol0273708
Abstract
[reaction: see text] We describe a catalytic asymmetric synthesis of both syn- and anti-3,5-dihydroxy esters. The method relies upon catalytic asymmetric epoxidation of alpha,beta-unsaturated imidazolides and amides, using lanthanide-BINOL complexes, and diastereoselective reduction of ketones. The method was applied to the enantioselective syntheses of 1,3-polyol/alpha-pyrone natural products 9a, 9b, and strictifolione (10). The absolute stereochemistry of 9a and 9b was also determined.Keywords
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