Issue 11, 2008

A stereodivergent synthesis of β-hydroxy-α-methylene lactonesviavinyl epoxides

Abstract

A catalytic diastereoselective sulfonium ylide epoxidation of aldehydes furnished original vinyl epoxides, having an MBH backbone. These highly functionalised building blocks were used for a formal synthesis of the antibiotic conocandin, and opened up a stereodivergent route towards β-hydroxy-α-methylene lactones, core units of naturally occurring compounds. Under acidic conditions, the oxiranes were mainly transformed, with moderate to good yields, into transβ-hydroxy-α-methylene lactones. On the other hand, a user-friendly palladium-catalysed CO2insertion and cyclisation sequence gave the cisβ-hydroxy-α-methylene lactone counterparts along with an interesting cistrans equilibration of the π-allyl intermediates.

Graphical abstract: A stereodivergent synthesis of β-hydroxy-α-methylene lactonesvia vinyl epoxides

Supplementary files

Article information

Article type
Paper
Submitted
12 Feb 2008
Accepted
12 Mar 2008
First published
09 Apr 2008

Org. Biomol. Chem., 2008,6, 1981-1993

A stereodivergent synthesis of β-hydroxy-α-methylene lactonesvia vinyl epoxides

M. Davoust, F. Cantagrel, P. Metzner and J. Brière, Org. Biomol. Chem., 2008, 6, 1981 DOI: 10.1039/B802310G

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