INTRAMOLECULAR CONDENSATION OF STEROIDAL 17-ALPHA-FORMYL 17-BETA-ACETATES - MODEL STUDIES ON 19-NORSTEROIDS, AND A ROUTE TO 3-METHOXY-19-NOR-17-ALPHA-PREGNA-1,3,5(10)-TRIENE-21,17-CARBOLACTONE

被引：10

作者：

BULL, JR

STEER, LM

机构：

[1] Department of Chemistry, University of Cape Town, Rondebosch

来源：

TETRAHEDRON | 1990年 / 46卷 / 15期

关键词：

D O I：

10.1016/S0040-4020(01)87846-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methods are described for the conversion of estrone 3-methyl ether (1) into 17β-acetoxy-3-methoxyestra-1,3,5(10)-triene-17α-carbaldehyde (5), treatment of which with lithium 2,2,6,6-tetramethylpiperidide at -100°C results in efficient intramolecular condensation to 20(R)-hydroxy-3-methoxy-19-nor-17α-pregna-1,3,5(10)-triene-21,17-carbolactone (14), which is converted into the title compound (16). The synthesis and base-mediated treatment of 17α-(toluene-p-sulphonyloxy-methyl)-3-methoxyestra-1,3,5(10)-trien-17β-yl-acetate (22) are described. © 1990.

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页码：5389 / 5400

页数：12

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