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Synlett 1998; 1998(8): 869-872
DOI: 10.1055/s-1998-1803
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A Synthesis of Mycalamide B

Philip J. Kocienski* , Robert Narquizian, Piotr Raubo, Christopher Smith, F. Thomas Boyle
  • *Department of Chemistry, Glasgow University, Glasgow G12 8QQ, UK
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Publication History

Publication Date:
31 December 2000 (online)

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Mycalamide B, a potent antitumour agent, was synthesized from cheap, readily available starting materials: ethyl lactate, ethyl isobutyrate, 4-chlorobutanal, and 4-chlorobutanoyl chloride. The trioxabicyclo[4.4.0]decane ring system was created by reaction of a methoxymethyl ether with a silyloxyoxirane induced by phosphorus pentoxide.

antitumour - 1,3-dioxane - conjugate addition - asymmetric hydrogenation - dihydroxylation - directed aldol - Curtius rearrangement - copper(I)