EFFICIENT DEGRADATION OF FK-506 TO A VERSATILE SYNTHETIC INTERMEDIATE

被引：16

作者：

ASKIN, D

JOE, D

REAMER, RA

VOLANTE, RP

SHINKAI, I

机构：

[1] Department of Process Research, Merck Sharp & Dohme Research Laboratories, Rahway, New Jersey 07065

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 20期

关键词：

D O I：

10.1021/jo00307a014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An 11-step degradation of natural FK-506 (1) to selectively protected C10-C34 synthetic intermediate 2 has been accomplished in 14% overall yield. The key steps include: (a) lead tetraacetate mediated C9-C10 bond cleavage of 24,32-bis(triisopropylsilyl)-FK-506 (3), (b) simultaneous C10 ester, C22 ketone reduction/C26 oxygen deacylation, and (c) selective bis(triethylsilylation) of the resulting triols 7a, b. The degradate 2 is ready for reacylation at the C26 hydroxyl terminus; hydrolysis of the dimethyl acetal moiety then provides an aldehyde ready for homologation at the C10 terminus. © 1990, American Chemical Society. All rights reserved.

引用

页码：5451 / 5454

页数：4

共 15 条

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