Approach to the synthesis of the C1–C11 and C14–C18 portion of Leucascandrolide A‡
Literature Information
Publication Date
2016-07-12
DOI
10.1039/C6QO00284F
Impact Factor
5.281
Authors
T. J. Hunter, J. Zheng, G. A. O'Doherty
View Original
Abstract
An asymmetric synthesis of the C1 to C11 and C14 to C18 fragments of the macrocyclic portion of the antibiotic Leucascandrolide A was achieved in 21 total steps from an achiral dienoate. The key 4-hydroxy-2,5-pyran portion of the natural product was established by oxy-Michael cyclization of a 5,7,9,11-tetraol intermediate, which in turn was established by an iterative asymmetric-hydration of dienoates. Alternative strategies for establishing the polyol stereochemistry were explored.
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Organic Chemistry Frontiers
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