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 - 2006 Aug 14
Externally publishedYes

Fingerprint

Macrolides
Glycosides
Glycosylation
Bromine
Lactones
Ether
Acids
auriside A
auriside B
pantolactone
glycidyl ethers

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Suenaga, K., Hoshino, H., Yoshii, T., Mori, K., Sone, H., Bessho, Y., ... 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

Enantioselective synthesis of aurisides A and B, cytotoxic macrolide glycosides of marine origin. / Suenaga, Kiyotake; Hoshino, Hiroshi; Yoshii, Takanori; Mori, Kazunori; Sone, Hiroki; Bessho, Yuhki; Sakakura, Akira; Hayakawa, Ichiro; Yamada, Kiyoyuki; Kigoshi, Hideo.

In: Tetrahedron, Vol. 62, No. 33, 14.08.2006, p. 7687-7698.

Research output: Contribution to journalArticle

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, vol. 62, no. 33, pp. 7687-7698. https://doi.org/10.1016/j.tet.2006.05.077
Suenaga, Kiyotake ; Hoshino, Hiroshi ; Yoshii, Takanori ; Mori, Kazunori ; Sone, Hiroki ; Bessho, Yuhki ; Sakakura, Akira ; Hayakawa, Ichiro ; Yamada, Kiyoyuki ; Kigoshi, Hideo. / Enantioselective synthesis of aurisides A and B, cytotoxic macrolide glycosides of marine origin. In: Tetrahedron. 2006 ; Vol. 62, No. 33. pp. 7687-7698.
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