ZINC(II)-CHLORIDE INDUCED THIOALKYLATION OF ALUMINUM ENOLATES - ENANTIOSELECTIVE SYNTHESIS OF ESTRADIOL-3-METHYL-17-TERT-BUTYL DIETHER

被引:21
作者
GROTH, U
KOHLER, T
TAAPKEN, T
机构
[1] Institut für Organische Chemie der Universität Göttingen, D-3400 Göttingen
关键词
D O I
10.1016/S0040-4020(01)88282-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Zinc(II)-chloride induced thioalkylation of the aluminium enolate 6 generated by conjugate reduction of the enone 5 leads - directly or via its trimethylsilylenol ether 6 - to alkylated hydrindanones 10 which are important intermediates in the synthesis of 19-norsteroids such as the title compound estradiol-3-methyl-17-tert-butyl diether 12.
引用
收藏
页码:7583 / 7592
页数:10
相关论文
共 22 条
[1]   NOVEL TOTAL SYNTHESES OF (+)-ESTRONE 3-METHYL ETHER, (+)-13BETA-ETHYL-3-METHOXYGONA-1,3,5(10)-TRIEN-17-ONE, AND (+)-EQUILENIN 3-METHYL ETHER [J].
COHEN, N ;
BANNER, BL ;
EICHEL, WF ;
PARRISH, DR ;
SAUCY, G ;
CASSAL, JM ;
MEIER, W ;
FURST, A .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (06) :681-685
[2]  
DANIEWSKI AR, 1988, LIEBIGS ANN CHEM, P593
[3]   A FACILE TOTAL SYNTHESIS OF ESTROGENS [J].
DANIEWSKI, AR ;
KIEGIEL, J .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) :5535-5538
[4]  
DANIEWSKI AR, 1989, LIEBIGS ANN CHEM, P1061
[5]  
DANIEWSKI AR, 1988, SYNTHETIC COMMUN, V18, P115
[6]  
DANIEWSKI AR, 1990, TETRAHEDRON LETT, P5599
[7]   TOTAL SYNTHESIS OF OPTICALLY ACTIVE STEROIDS .6. NEW TYPE OF ASYMMETRIC CYCLIZATION TO OPTICALLY ACTIVE STEROID CD PARTIAL STRUCTURES [J].
EDER, U ;
SAUER, G ;
WEICHERT, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (07) :496-&
[8]  
EDER U, 1976, CHEM BER, V40, P681
[9]  
GROTH U, UNPUB LIEBIGS ANN CH
[10]   ASYMMETRIC SYNTHESIS OF BICYCLIC INTERMEDIATES OF NATURAL PRODUCT CHEMISTRY [J].
HAJOS, ZG ;
PARRISH, DR .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (12) :1615-1621