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

被引：17
作者：
Suenaga, Kiyotake
Hoshino, Hiroshi
Yoshii, Takanori
Mori, Kazunori
Sone, Hiroki
Bessho, Yuhki
Sakakura, Akira
Hayakawa, Ichiro
Yamada, Kiyoyuki
Kigoshi, Hideo
机构：
[1] Univ Tsukuba, Dept Chem, Tsukuba, Ibaraki 3058571, Japan
[2] Nagoya Univ, Grad Sch Sci, Chikusa Ku, Nagoya, Aichi 4648602, Japan
来源：
TETRAHEDRON | 2006年 / 62卷 / 33期
关键词：
D O I：
10.1016/j.tet.2006.05.077
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7687 / 7698
页数：12
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