PREPARATION OF 16-FORMYLESTRADIOL AND THE 16-(ALPHA-METHYLENEBUTANOLIDE) DERIVATIVE

被引：5

作者：

AKANNI, OA

MARPLES, BA

机构：

[1] Department of Chemistry, University of Technology, Oughborough, Leicestershire England

来源：

STEROIDS | 1993年 / 58卷 / 05期

关键词：

STEROIDS; ESTROGENS; 16-FORMYLESTRADIOL; BUTANOLIDE; METHYL ALPHA-(BROMOMETHYL)ACRYLATE;

D O I：

10.1016/0039-128X(93)90025-I

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Routes to the preparation of 16-formylestradiol are described. Estrone was converted to (E)-16-methoxymethylene estrone via the 16-hydroxymethylene estrone. Reduction of the methoxymethylene estrone with NaBH4 in the presence of CeCl3 gave 16-methoxymethylene estradiol. Deprotection by acid afforded the desired 16-formylestradiol. Attempts to prepare the 16- formylestradiol via the 16-butylthiomethylene derivative gave only 16-formylestra-1,3,5(10),16-tetraen-3-ol, and a route through the 16-dimethoxymethyl derivative gave a mixture of the 16-formyltetraen-3-ol and the 16-formylestradiol in low yield. The 16-formylestradiol was subsequently converted to the alpha-methylene lactone conjugate, 4-(3,17beta-dihydroxyestra-1,3,5(10)trien-16-yl)-2-methylene4-butanolide by reaction with methyl alpha-(bromomethyl) acrylate and zinc.

引用

页码：234 / 238

页数：5

共 19 条

[1]

BERNSTEIN PR, 1979, TETRAHEDRON LETT, V12, P1015

[2] SYNTHESIS AND CYTO-TOXIC ACTIVITY OF ESTROGEN ALPHA-METHYLENE-DELTA-LACTONES [J].