BICYCLO(3.4.0)NON-1-ENE DERIVATIVES - SYNTHESIS OF DES-A-PREGN-9-ENE-3,20-DIONE

被引：13

作者：

BRUNKE, EJ

BIELSTEIN, H

KUTSCHAN, R

REHME, G

SCHUETZ, HJ

WOLF, H

机构：

[1] TECH UNIV BRUNSWICK,INST ORGAN CHEM,D-3300 BRUNSWICK,FED REP GER

[2] GESELL BIOTECHNOL FORSCH MBH,D-3300 BRUNSWICK,FED REP GER

来源：

TETRAHEDRON | 1979年 / 35卷 / 13期

关键词：

D O I：

10.1016/0040-4020(79)80023-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclization of the allylic alcohols 12,17 and 22 easily obtainable from Hagemann's ester (2 or 1) via the cyclohexenone derivatives 7 and 10 was investigated with regard to steroid syntheses of the pregnane series. The 6,7-cis-tetrahydroindane derivatives 16a and 23 are formed stereoselectively by acid catalyzed cyclization of 12 or 22; ring closure of 22 occurs largely regioselectively. Cyclization of 17 yields selectively the 6,7-cis (18a) or 6,7-trans compound (18b). Des-A-pregn-9-en-3,20-dion (28a) was obtained by allylic oxidation of 23, subsequent hydrogenation and aldol condensation. © 1979.

引用

页码：1607 / 1613

页数：7

共 44 条

[41] ALKYLATION OF HAGEMANNS ESTER - PREPARATION OF AN INTERMEDIATE FOR TRISPORIC ACID SYNTHESIS [J].