CYCLOADDITION OF PHENYL VINYL SULFONE TO 3-METHOXY-16-METHYLESTRA-1,3,5(10),14,16-PENTAEN-17-YL ACETATE - SYNTHESIS OF 14-FUNCTIONALIZED 19-NORPREGNANE DERIVATIVES

被引：20

作者：

BULL, JR

BISCHOFBERGER, K

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 11期

关键词：

D O I：

10.1039/p19910002859

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diels-Alder reaction of 3-methoxy-16-methylestra-1,3,5(10),14,16-pentaen-17-yl acetate 3 with phenyl vinyl sulphone affords three 14,17-cycloadducts; the two major products (ca. 37% each) are the regioisomers derived from endo addition on the beta-face, whereas the minor product (ca. 14%) is the endo isomer of meta-directed attack on the alpha-face. Sequential reductive desulphonylation, hydroxylation, and oxidative cleavage of the major products is described, and the derived 14-hydroxymethyl-3-methoxy-19-norpregna-1,3,5(10)-trien-20-one 16 is converted into 14-alpha-hydroxymethyl and 14-alpha-formyl analogues of 19-norprogesterone. A route to 3-methoxy-14-methyl-19-norpregna-1,3,5(10)-trien-20-one 27 is described.

引用

页码：2859 / 2865

页数：7

共 14 条

[1]

ATWAL KS, 1982, HETEROCYCLES, V19, P641

[2] 14-METHYL STEROIDS .5. STRUCTURAL FEATURES INFLUENCING STEREOSELECTIVITY OF 14-METHYLATION OF 15-OXO-19-NORSTEROIDS - SYNTHESIS OF 14-ALPHA-METHYL-19-NORPROGESTERONE [J].