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

doi:10.1016/j.tet.2006.05.077

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 journal › Article

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 language	English
Pages (from-to)	7687-7698
Number of pages	12
Journal	Tetrahedron
Volume	62
Issue number	33
DOIs	https://doi.org/10.1016/j.tet.2006.05.077
Publication status	Published - 2006 Aug 14
Externally published	Yes

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

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 journal › Article

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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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AU - Yoshii, Takanori

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AU - Sone, Hiroki

AU - Bessho, Yuhki

AU - Sakakura, Akira

AU - Hayakawa, Ichiro

AU - Yamada, Kiyoyuki

AU - Kigoshi, Hideo

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