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Tandem enantioselective conjugate addition-cyclopropanation. Application to natural product synthesis

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Published in Journal of Organic Chemistry. 2002, vol. 67, no. 25, p. 8753-8757
Abstract A tandem asymmetric conjugate addition-cyclopropanation was developed, in which a cyclic or linear enone was converted to a TMS-protected 3-substituted-cyclopropanol in an efficient one-pot reaction. These compounds were then selectively cleaved to yield alpha-methyl-beta-alkyl ketones, alpha-methylene-enones, or chain extended gamma-alkyl-enones. This methodology was applied to the formal total synthesis of (-)-(S,S)-clavukerin A and (+)-(R,S)-isoclavukerin.
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PMID: 12467385
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ALEXAKIS, Alexandre, MARCH, Sebastien. Tandem enantioselective conjugate addition-cyclopropanation. Application to natural product synthesis. In: Journal of Organic Chemistry, 2002, vol. 67, n° 25, p. 8753-8757. https://archive-ouverte.unige.ch/unige:8030

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Deposited on : 2010-06-21

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