Asymmetric Synthesis of Quaternary Centers. Total Synthesis of (−)-Malyngolide
- 18 November 2000
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (25) , 4013-4015
- https://doi.org/10.1021/ol006599p
Abstract
The deracemization of 3-nonyl-3,4-epoxybut-1-ene with Pd(0) in the presence of chiral ligands using p-methoxybenzyl alcohol as a nucleophile proceeds regio- and enantioselectively to form the monoprotected vinylglycidol in 99% ee. This chiral building block was converted in seven steps to (−)-malyngolide, an antibiotic showing significant activity against Mycobacterium smegmatis and Streptococcus pyogenes. An interesting aspect involves controlling the diastereoselectivity of protonation of an enolate via a distal hydroxyl group.Keywords
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