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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