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Synlett 1991; 1991(1): 58-60
DOI: 10.1055/s-1991-20629
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Radical Cyclization of (Bromomethyl)dimethylsilyl Propargyl Ethers; III. Stereoselective Hydrogen Abstraction of Trisubstituted Vinyl Radicals. Application to a Terpenoid Building Block Synthesis1

Michel Journet* , Elisabeth Magnol, William Smadja, Max Malacria
  • *Université Pierre et Marie Curie - Paris VI - Laboratoire de Chimie Organique de Synthèse, URA 408, Tour 44-54, 4 Place Jussieu, F-75252 Paris Cedex 05, France
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Publication Date:
07 March 2002 (online)

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Trisubstituted olefins have been obtained via stereoselective hydrogen abstraction by vinyl radicals, prepared by the radical cyclization of (bromomethyl)dimethylsilyl propargyl ethers. Application to the stereoselective synthesis of the terpenoid building block (Z)-2-methyl-7-(2-tetrahydropyranyloxy)-3-(trimethylsilylmethyl)-3-hepten-2-ol, prepared by the radical cyclization of 2-[(bromomethyl)dimethylsiloxy)-2-methyl-7-(2-tetrahydropyranyloxy)-3-heptyne, is given to illustrate the methodology.

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