Synthesis of 2,6-cis-disubstituted 4-methylenetetrahydropyrans by oxy-Michael addition

Duncan Gill, Nicholas H. Taylor, Eric J. Thomas

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The combination of an 'ene' reaction between a 2-(2-trialkylsilyloxyalkyl) prop-2-enyl(trimethyl)silane and an alk-1-yn-3-one mediated by zinc(II) iodide, and an intramolecular oxy-Michael reaction, provides an efficient synthesis of cis-2,6-disubstituted 4-methylenetetrahydropyrans of interest in the context of a synthesis of bryostatins. The stereoselective formation of (E)-vinylsilanes in the 'ene' reaction is of interest.

Original languageEnglish
Pages (from-to)5034-5045
Number of pages12
JournalTetrahedron
Volume67
Issue number27-28
Early online date16 Apr 2011
DOIs
Publication statusPublished - 8 Jul 2011
Externally publishedYes

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