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Enantioselective synthesis of aurisides A and B, cytotoxic macrolide glycosides of marine origin
Authors:Kiyotake Suenaga  Hiroshi Hoshino  Kazunori Mori  Yuhki Bessho  Ichiro Hayakawa  Hideo Kigoshi
Institution:a Department of Chemistry, University of Tsukuba, 1-1-1 Tennoudai, Tsukuba, Ibaraki 305-8571, Japan
b Graduate School of Sciences, Nagoya University, Chikusa, Nagoya 464-8602, Japan
Abstract:The enantioselective synthesis of aurisides A and B, macrolide glycosides of marine origin, was achieved by a convergent approach. The C1-C9 segment 4 was prepared from (R)-pantolactone, and the C10-C17 segment 14 was synthesized from (R)-glycidyl trityl ether. The Nozaki-Hiyama-Kishi reaction between 4 and 14 and subsequent reactions gave seco acid 10, which was converted into the aglycon (3) of aurisides by construction of the 14-membered lactone and bromine-substituted conjugated diene. The glycosylation reaction of the aglycon provided aurisides A and B.
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