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Communication | Special issue | Vol 76, No. 2, 2008, pp.1069-1074
Published online, 19th June, 2008
DOI: 10.3987/COM-08-S(N)113
Stereoselective Synthesis of Maitotoxin GHI-Ring System Having a 1,2-Diol Side Chain

Masanori Nagatomo and Tadashi Nakata*

*Department of Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan


The stereoselective synthesis of maitotoxin GHI-ring system having a 1,2-diol side chain was accomplished via successive SmI2-induced reductive cyclizations of β-alkoxyacrylate-aldehyde and optically active (E)-β-alkoxyvinylsulfoxide-aldehyde, dihydroxylation of α,β-unsaturated δ-lactone, and Sharpless asymmetric dihydroxylation of the side chain.