Total synthesis of (R)-telomestatin

被引：103

作者：

Doi, Takayuki

Yoshida, Masahito

Shin-ya, Kazuo

Takahashi, Takashi

机构：

[1] Tokyo Inst Technol, Dept Appl Chem, Tokyo 1528552, Japan

[2] Univ Tokyo, Inst Mol & Cellular Biosci, Bunkyo Ku, Tokyo 1130032, Japan

[3] Natl Inst Adv Ind Sci & Technol, Biol Informat Res Ctr, Prot Network Team, Low MW Chem Lab,Koto Ku, Tokyo 1350064, Japan

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 18期

关键词：

D O I：

10.1021/ol061793i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have achieved a total synthesis of telomestatin, and its absolute configuration was determined to be (R). Coupling of cysteine-containing trisoxazole amine and serine-containing trisoxazole carboxylic acid, followed by macrocyclization, provided a 24-membered diamide. The seventh oxazole ring was formed by a Shin's procedure via dehydroamide. Cyclodehydration of a modified (R)-cysteine-(S-Bu-t) moiety using Kelly's method (PPh3(O)-Tf2O) with anisole furnished (R)-telomestatin, whose CD spectrum was in good agreement with that of the natural product.

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页码：4165 / 4167

页数：3

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