APPLICATION OF SUBSTITUENT-CONTROLLED OXIDATIVE COUPLING OF GLYCALS IN A SYNTHESIS AND STRUCTURAL CORROBORATION OF CICLAMYCIN-0 - NEW POSSIBILITIES FOR THE CONSTRUCTION OF HYBRID ANTHRACYCLINES

被引：61

作者：

SUZUKI, K ^{[1
]}

SULIKOWSKI, GA ^{[1
]}

FRIESEN, RW ^{[1
]}

DANISHEFSKY, SJ ^{[1
]}

机构：

[1] YALE UNIV,DEPT CHEM,NEW HAVEN,CT 06511

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1990年 / 112卷 / 24期

关键词：

D O I：

10.1021/ja00180a037

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A synthesis of ciclamycin 0 (1) has been achieved. The required trisaccharide glycal 14 was assembled by substituent-directed iodinative coupling of glycals (see 2 + 3 → 5 and 2 + 7 → 8). The key anthracycline-trisaccharide attachment was effected by iodinative coupling of ϵ-pyrromycinone (15) with 14. In addition to the expected diaxial product, 16 this reaction gave rise to considerable amounts of the axial glycoside-equatorial iodide product 17 as well as traces of 1,2-diequatorial product. The two major series converged upon de-iodination leading to ciclamycin 0. By employing a similar iodinative coupling of daunomycinone 21 and 14, this time with improved diaxial stereoselectivity, the ciclamycin-daunomycin hybrid 26 was eventually synthesized. © 1990, American Chemical Society. All rights reserved.

引用

页码：8895 / 8902

页数：8

共 46 条

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