VITAMIN-B12, A CATALYST IN THE SYNTHESIS OF PROSTAGLANDINS

被引：78

作者：

BUSATO, S ^{[1
]}

TINEMBART, O ^{[1
]}

ZHANG, ZD ^{[1
]}

SCHEFFOLD, R ^{[1
]}

机构：

[1] UNIV BERN, INST ORGAN CHEM, FREIESTR 3, CH-3012 BERN, SWITZERLAND

来源：

TETRAHEDRON | 1990年 / 46卷 / 09期

关键词：

D O I：

10.1016/S0040-4020(01)85455-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A prostaglandin F2α precursor containing all structural features from C6 to C20 with 8R, 9S, 11R and 12R chirality is obtained by the one step formation of two C-C bonds in the B12-catalyzed radical cyclization-addition sequence starting from a chiral cyclopentene bromoacetal and l-octyne-3-one. The B12-catalyzed radical cyclization-elimination sequence of a chiral cyclopentene precursor leads to (-)-(3aR,6aS)-3,3a,6,6a-tetrahydro-2H-cyclopenta abfuran-2-one. Its (+)-(3aS,6aR-enantiomer is obtained via B12-catalyzed, enantio- selective isomerization of cyclopentene oxide to (R)-2-cyclopentene-l-ol followed by the B12-catalyzed radical cyclization-elimination sequence of its bromoacetal. © 1990.

引用

页码：3155 / 3166

页数：12

共 65 条

[1] VITAMIN-B12 COENZYME [J].

ABELES, RH ;

DOLPHIN, D .

ACCOUNTS OF CHEMICAL RESEARCH, 1976, 9 (03) :114-120

[2]

BARRERE G, 1981, SCIENCE, P56

[3] REGIO-SELECTIVITY AND STEREO-SELECTIVITY IN RADICAL REACTIONS [J].

BECKWITH, ALJ .

TETRAHEDRON, 1981, 37 (18) :3073-3100

[4]

BINDRA JS, 1977, PROSTAGLANDIN SYNTHE, P71

[5]

COREY EJ, 1970, TETRAHEDRON LETT, P307

[6] NEW STEREOCONTROLLED SYNTHESIS OF PROSTAGLANDINS VIA PROSTAGLANDIN A2 [J].

COREY, EJ ;

MANN, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (20) :6832-6833

[7]

COREY EJ, 1970, TETRAHEDRON LETT, P311

[8]

COREY EJ, 1974, TETRAHEDRON LETT, P2439

[9] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].

COREY, EJ ;

VENKATESWARLU, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+

[10]

CURRAN DP, 1990, IN PRESS COMPREHENSI, V4

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