Tetrahedron

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

D Gill, NH Taylor, EJ Thomas

Index: Gill, Duncan; Taylor, Nicholas H.; Thomas, Eric J. Tetrahedron, 2011 , vol. 67, # 27-28 p. 5034 - 5045

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Citation Number: 4

Abstract

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.

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