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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Bryostatins
Silanes
Iodides
Zinc
zinc iodide
vinylsilane

Cite this

Gill, Duncan ; Taylor, Nicholas H. ; Thomas, Eric J. / Synthesis of 2,6-cis-disubstituted 4-methylenetetrahydropyrans by oxy-Michael addition. In: Tetrahedron. 2011 ; Vol. 67, No. 27-28. pp. 5034-5045.
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Synthesis of 2,6-cis-disubstituted 4-methylenetetrahydropyrans by oxy-Michael addition. / Gill, Duncan; Taylor, Nicholas H.; Thomas, Eric J.

In: Tetrahedron, Vol. 67, No. 27-28, 08.07.2011, p. 5034-5045.

Research output: Contribution to journalArticle

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AU - Gill, Duncan

AU - Taylor, Nicholas H.

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