AN EFFICIENT ASYMMETRIC-SYNTHESIS OF 1-ALPHA,25-(OH)2 VITAMIN-D3 A-RING SYNTHON

被引：39

作者：

NAGASAWA, K ^{[1
]}

ISHIHARA, H ^{[1
]}

ZAKO, Y ^{[1
]}

SHIMIZU, I ^{[1
]}

机构：

[1] WASEDA UNIV,SCH SCI & ENGN,DEPT APPL CHEM,OOKUBO 3-4-1,SHINJUKU KU,TOKYO 169,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 09期

关键词：

D O I：

10.1021/jo00061a028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral synthesis of the A-ring synthon 3 of 1alpha,25-dihydroxyvitamin D3 (1a) based on palladium-catalyzed cyclization of 8-bromo-2,8-nonadienoates is described. Reaction of (E)-4b and (Z)-4d in the presence of Pd(OAc)2, PPh3, and K2CO3 gave (E)-3b and (Z)-3d, respectively. Optically active 4d was prepared from 24 by asymmetric aldol reaction using 31, which was cyclized to 3d. With further reactions, 1alpha,25-dihydroxyvitamin D3 (1a) was obtained.

引用

页码：2523 / 2529

页数：7

共 37 条

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