REVISED STEREOSTRUCTURE FOR (+)-ROEMECARINE AND SYNTHESIS OF (+/-)-ROEMECARINE, (+)-ROEMECARINE, AND (-)-ROEMECARINE AND (+/-)-EPIROEMECARINE

被引：6

作者：

HOSHINO, O ^{[1
]}

ITOH, K ^{[1
]}

TANAHASHI, R ^{[1
]}

UMEZAWA, B ^{[1
]}

AKITA, H ^{[1
]}

OISHI, T ^{[1
]}

机构：

[1] RIKEN INST PHYS & CHEM RES, WAKO, SAITAMA 35101, JAPAN

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1990年 / 38卷 / 12期

关键词：

(+)-ROEMECARINE; (+/-)-ROEMECARINE; (+/-)-EPIROEMECARINE; (-)-ROEMECARINE; (+/-)-4-O-ACETYLROEMECARINE; (+/-)-4,6-O,O-DIACETYLROEMECARINE; KINETIC RESOLUTION; IMMOBILIZED LIPASE OF-360; CANDIDA-CYLINDRACEA; ISOOCTANE;

D O I：

10.1248/cpb.38.3277

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The stereostructure of (+)-roemecarine, a new 1-benzyl-1,2,3,4-tetrahydroisoquinoline having a hydroxyl group at the 4-position, was confirmed to be 1,4-trans by synthesis of (+/-)-epiroemecarine (1) and (+/-)-roemecarine (5) via omicron-quinol acetates of isocodamine (4). Furthermore, (+/-)-and (-)-roemecarine (5) were synthesized in good chemical and optical yields by kinetic resolution of (+/-)-4-O-acetyl- (3) or (+/-)-4,6-O,O-diacetylroemecarine (7) by the use of immobilized lipase OF-360 (Candida cylindracea) in organic solvents. (+)-Roemecarine (5) was proved to have 1S,4S-configuration.

引用

页码：3277 / 3279

页数：3

共 7 条

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