Synthesis of the Pluramycins 1: Two Designed Anthrones as Enabling Platforms for Flexible Bis-C-Glycosylation

被引：38

作者：

Kitamura, Kei ^{[1
]}

Ando, Yoshio ^{[1
]}

Matsumoto, Takashi ^{[2
]}

Suzuki, Keisuke ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Chem, Meguro Ku, Tokyo 1528551, Japan

[2] Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 05期

关键词：

amino sugars; bis-C-glycosides; C-glycosylation; Lewis acids; pluramycins; ARYL GLYCOSIDES; BIOSYNTHESIS; DERIVATIVES; HEDAMYCIN; DNA;

D O I：

10.1002/anie.201308016

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two effective tricyclic platforms are reported for the installation of the two constituent sugars, L-vancosamine and D-angolosamine, in a regio- and stereoselective manner for the synthesis of the pluramycin class of bis-C-glycoside antitumor antibiotics. Two complementary protocols are now available that differ in the order in which the two sugar moieties are installed. Sc(OTf)(3) was effective as the Lewis acid.

引用

页码：1258 / 1261

页数：4