STEREOSELECTIVE TOTAL SYNTHESIS OF TESTOSTERONE AND ANDROSTERONE VIA A/B-RING CONSTRUCTION OF THE STEROIDAL RING-SYSTEM BY INTRAMOLECULAR DIELS-ALDER REACTION

被引:30
作者
IHARA, M
SUDOW, I
FUKUMOTO, K
KAMETANI, T
机构
[1] TOHOKU UNIV,INST PHARMACEUT,SENDAI,MIYAGI 980,JAPAN
[2] HOSHI UNIV,INST MED CHEM,SHINAGAWA KU,TOKYO 142,JAPAN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1986年 / 01期
关键词
D O I
10.1039/p19860000117
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:117 / 123
页数:7
相关论文
共 32 条
[1]   STEROIDS - CCV. RING A MODIFIED HORMONE ANALOGS. .1. SOME RING A OLEFINS [J].
BOWERS, A ;
CROSS, AD ;
DENOT, E ;
CALZADA, MC ;
CARPIO, H ;
EDWARDS, A .
JOURNAL OF MEDICINAL CHEMISTRY, 1963, 6 (02) :156-&
[2]  
BUCHI G, 1969, J ORG CHEM, V34, P1122
[3]   HYDROBORATION .5. NEW SYNTHESIS OF ANDROSTERONE + 19-NORANDROSTERONE [J].
CAGLIOTI, L ;
MAINA, G ;
SELVA, A ;
CAINELLI, G .
TETRAHEDRON, 1964, 20 (04) :957-&
[4]   THE INTRAMOLECULAR DIELS-ALDER REACTION - RECENT ADVANCES AND SYNTHETIC APPLICATIONS [J].
FALLIS, AG .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (02) :183-234
[5]   ALDEHYDES AND KETONES FROM THIOACETALS [J].
FETIZON, M ;
JURION, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (07) :382-&
[6]   HARD ACID AND SOFT NUCLEOPHILE SYSTEM - NEW EFFICIENT METHOD FOR REMOVAL OF BENZYL PROTECTING GROUP [J].
FUJI, K ;
ICHIKAWA, K ;
NODE, M ;
FUJITA, E .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (10) :1661-1664
[7]   THERMAL, PHOTOCHEMICAL, AND TRANSITION-METAL MEDIATED ROUTES TO STEROIDS BY INTRAMOLECULAR DIELS-ALDER REACTIONS OF ORTHO-XYLYLENES (ORTHO-QUINODIMETHANES) [J].
FUNK, RL ;
VOLLHARDT, KPC .
CHEMICAL SOCIETY REVIEWS, 1980, 9 (01) :41-61
[8]  
HAJOS ZG, 1967, J ORG CHEM, V32, P3008
[9]   ASYMMETRIC SYNTHESIS OF BICYCLIC INTERMEDIATES OF NATURAL PRODUCT CHEMISTRY [J].
HAJOS, ZG ;
PARRISH, DR .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (12) :1615-1621
[10]   TOTAL SYNTHESIS OF OPTICALLY ACTIVE (-)17BETA-HYDROXY-DELTA9(10)-DESA-ANDROSTEN-5-1 [J].
HAJOS, ZG ;
PARRISH, DR ;
OLIVETO, EP .
TETRAHEDRON, 1968, 24 (04) :2039-&