HYDROBORATION OF C-ARYLGLUCALS - SYNTHESIS OF THE BETA-C-ARYLGLUCOSIDE NUCLEUS OF CHAETIACANDIN

被引：40

作者：

FRIESEN, RW

DALJEET, AK

机构：

[1] Department of Chemistry, University of Toronto, Lash Miller Chemical Laboratories, Toronto, Ont. M5S 1A1

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 43期

关键词：

D O I：

10.1016/S0040-4039(00)97006-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hydroborations of the C-arylglucals 3a-c obtained from palladium catalyzed coupling reactions, provide the corresponding β-C-arylglucosides. Depending upon the conditions chosen for the oxidative workup, either the alcohols 5a-c or the products resulting from silyl migration (4a-c) are readily obtained. The palladium catalyzed coupling-hydroboration sequence has been applied to the synthesis of the β-C-arylglucoside nucleus of chaetiacandin, an anti-yeast antibiotic of the papulacandin family. © 1990.

引用

页码：6133 / 6136

页数：4

共 12 条

[1]

BROWN HC, 1974, SYNTHESIS-STUTTGART, P77

[2]

CRAGG GML, 1973, ORGANOBORANES ORGANI

[3] THE PREPARATION OF C-ARYLGLYCALS - THE PALLADIUM-CATALYZED COUPLING OF 3,4,6-TRI-O-(TERT-BUTYLDIMETHYLSILYL)-1-(TRIBUTYLSTANNYL)-D-GLUCAL AND ARYL BROMIDES [J].