A total synthesis of the natural product microcarpalide is described. Ring-closing metathesis of a dienic ester was used as the key step. Mannose was used as the chiral pool material for the construction of the olefinic-acid and a Sharpless asymmetric dihydroxylation reaction provided the chiral precursor for the synthesis of the olefinic-alcohol. (C) 2003 Elsevier Science Ltd. All rights reserved.
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Univ Tokyo, Grad Sch Agr & Life Sci, Dept Appl Biol Chem, Bunkyo Ku, Tokyo 1138657, JapanUniv Tokyo, Grad Sch Agr & Life Sci, Dept Appl Biol Chem, Bunkyo Ku, Tokyo 1138657, Japan
Ishigami, K
Watanabe, H
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Univ Tokyo, Grad Sch Agr & Life Sci, Dept Appl Biol Chem, Bunkyo Ku, Tokyo 1138657, JapanUniv Tokyo, Grad Sch Agr & Life Sci, Dept Appl Biol Chem, Bunkyo Ku, Tokyo 1138657, Japan
Watanabe, H
Kitahara, T
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Univ Tokyo, Grad Sch Agr & Life Sci, Dept Appl Biol Chem, Bunkyo Ku, Tokyo 1138657, JapanUniv Tokyo, Grad Sch Agr & Life Sci, Dept Appl Biol Chem, Bunkyo Ku, Tokyo 1138657, Japan