TRANSFORMATION OF RESIN ABIETIC ACID INTO A PREGNANE-TYPE STEROID

被引:4
作者
ABAD, A
AGULLO, C
ARNO, M
DOMINGO, LR
ROZALEN, J
ZARAGOZA, RJ
机构
来源
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1991年 / 69卷 / 03期
关键词
ABIETIC ACID; PREGNANE STEROIDS; ACETYLENE-CATION CYCLIZATION;
D O I
10.1139/v91-058
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Abietic acid (1a) has been converted into the pregnane analogue steroid 10 via a sequence of transformations involving as key step the acetylene-cation cyclization of 9.
引用
收藏
页码:379 / 382
页数:4
相关论文
共 16 条
[1]   CONVERSION OF DEHYDROABIETIC ACID INTO 20-KETO-C-ARYL-18-NORSTEROIDS - FORMATION OF THE D-RING [J].
ABAD, A ;
AGULLO, C ;
ARNO, M ;
DOMINGO, LR ;
ZARAGOZA, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (16) :3761-3765
[2]   SYNTHESIS OF (+)-PODOCARP-8(14)-EN-13-ONE AND METHYL-(+)-13-OXO-PODOCARP-8(14)-EN-18-OATE FROM ABIETIC ACID [J].
ABAD, A ;
ARNO, M ;
DOMINGO, LR ;
ZARAGOZA, RJ .
TETRAHEDRON, 1985, 41 (21) :4937-4940
[3]   INTRAMOLECULAR ACYLATION OF SOME HEX- HEPT- AND OCT-ENOIC ACIDS [J].
ANSELL, MF ;
EMMETT, JC ;
COOMBS, RV .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (03) :217-&
[4]  
BERMEJO F, 1988, CAN J CHEM, V66, P2200
[5]   CHEMISTRY OF PODOCARPACEAE .47. STEROIDAL ANALOGS FROM 12-HYDROXYPODOCARPA-8,11,13-TRIEN-19-OIC ACID [J].
CAMBIE, RC ;
DENNY, WA ;
FULLERTO.TJ ;
HAYWARD, RC .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1974, 27 (06) :1317-1325
[6]  
DELMOND B, 1987, TETRAHEDRON LETT, V28, P2127
[7]   EFFICIENT SYNTHESIS OF A PREGNANE-TYPE STEROID - TOTAL SYNTHESIS OF (+)-5-ALPHA-DIHYDROPREGNENOLONE [(+)-3-BETA-HYDROXY-5-ALPHA-PREGNAN-20-ONE] [J].
KAMETANI, T ;
SUZUKI, K ;
NEMOTO, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (12) :2805-2807
[8]  
KAMETANI T, 1982, J ORG CHEM, V47, P2331, DOI 10.1021/jo00133a020
[9]   A STEREOCONTROLLED TOTAL SYNTHESIS OF 2-BETA,3-BETA,20-BETA-TRIACETOXY-5ALPHA-PREGNAN-6-ONE - A TOTAL SYNTHESIS OF 20-HYDROXYECDYSONE [J].
KAMETANI, T ;
TSUBUKI, M ;
NEMOTO, H .
TETRAHEDRON LETTERS, 1980, 21 (50) :4855-4856
[10]   MODEL STUDIES FOR STEROID C-D RING SYNTHESIS - STEREOSELECTIVE HYDRINDAN FORMATION BY MEANS OF ACETYLENE-CATION CYCLIZATION [J].
LANSBURY, PT ;
DEMMIN, TR ;
DUBOIS, GE ;
HADDON, VR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (02) :394-403