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.
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页码：5451 / 5454
页数：4
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