Enantioselective synthesis of aurisides A and B, cytotoxic macrolide glycosides of marine origin

Kiyotake Suenaga, Hiroshi Hoshino, Takanori Yoshii, Kazunori Mori, Hiroki Sone, Yuhki Bessho, Akira Sakakura, Ichiro Hayakawa, Kiyoyuki Yamada, Hideo Kigoshi

研究成果: Article査読

22 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)7687-7698
ページ数12
ジャーナルTetrahedron
62
33
DOI
出版ステータスPublished - 2006 8月 14
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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