A REMARKABLE GLYCOSYLATION REACTION - THE TOTAL SYNTHESIS OF CALICHEAMICIN GAMMA(1)

被引：46

作者：

HITCHCOCK, SA

CHUMOYER, MY

BOYER, SH

OLSON, SH

DANISHEFSKY, SJ

机构：

[1] SLOAN KETTERING INST CANC RES,BIOORGAN CHEM LAB,NEW YORK,NY 10021

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

[3] COLUMBIA UNIV,DEPT CHEM,NEW YORK,NY 10027

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1995年 / 117卷 / 21期

关键词：

D O I：

10.1021/ja00126a014

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An account of the reasoning and reduction to practice of a highly convergent total stereospecific synthesis of calicheamicin gamma(1)(I) (1) is provided. The key finding was the use of a very mild promoter system (silver triflate and 4 Angstrom molecular sieves in methylene chloride) to allow for coupling of trichloroacetimidate 21 with advanced calicheamicinone-like accepters (see 17 and 18). Glycosidation with 17 affords a 3:1 ratio of equatorial to axial glycosides. The use of 18 seems to afford only the equatorial beta-glycoside. Remarkably, use of the enantiomer of 17 as the acceptor gave an 18:1 ratio of axial to equatorial product.

引用

页码：5750 / 5756

页数：7

共 30 条

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