AN ENANTIOSELECTIVE VERSION OF THE AB+D-]ABCD- TYPE STEROID TOTAL SYNTHESIS

被引：44

作者：

QUINKERT, G

DELGROSSO, M

BUCHER, A

BAUCH, M

DORING, W

BATS, JW

DURNER, G

机构：

[1] Institut für Organische Chemie der Universität, D-6000 Frankfurt am Main 50, Niederurseler Hang

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 25期

关键词：

STEROID TOTAL SYNTHESIS; ENANTIOSELECTIVE LEWIS ACID-MEDIATED DIELS ALDER REACTION;

D O I：

10.1016/S0040-4039(00)92517-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diene 1 and dienophile 4a in a Diels/Alder reaction mediated by a chiral ligand-modified Lewis acid enantioselectively furnish adduct 5a (chem. yield. 64%, e.e.: 73%), which after partial deoxygenation and final enantioselection by recrystallization affords 5b. The latter compound can easily be converted via Torgov's pentaenone 6a into estrogens or progestogens.

引用

页码：3617 / 3620

页数：4

共 11 条

[1]

ANANCHENKO SN, 1963, TETRAHEDRON LETT, P1553

[2]

BLICKENSTAFF RT, 1974, TOTAL SYNTHESIS STER, pCH5

[3] A STEREOSELECTIVE TOTAL SYNTHESIS OF OESTRONE, AND RELATED STUDIES [J].