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

Research output: Contribution to journalArticle

22 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)7687-7698
Number of pages12
JournalTetrahedron
Volume62
Issue number33
DOIs
Publication statusPublished - Aug 14 2006
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Suenaga, K., Hoshino, H., Yoshii, T., Mori, K., Sone, H., Bessho, Y., Sakakura, A., Hayakawa, I., Yamada, K., & Kigoshi, H. (2006). Enantioselective synthesis of aurisides A and B, cytotoxic macrolide glycosides of marine origin. Tetrahedron, 62(33), 7687-7698. https://doi.org/10.1016/j.tet.2006.05.077