NOVEL STEROIDS FROM CETYLTRIMETHYLAMMONIUM PERMANGANATE-INITIATED OXIDATIVE REARRANGEMENTS OF 16-DEHYDROPROGESTERONE

被引：9

作者：

KYM, PR ^{[1
]}

WILSON, SR ^{[1
]}

GRITTON, WH ^{[1
]}

KATZENELLENBOGEN, JA ^{[1
]}

机构：

[1] UNIV ILLINOIS,DEPT CHEM,URBANA,IL 61801

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 18期

关键词：

D O I：

10.1016/S0040-4039(00)76637-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cetyltrimethylammonium permanganate initiates oxidative opening of the D-ring of 16-dehydroprogesterone in CH2Cl2. The novel steroids 3 and 4 have been isolated and characterized as the major products obtained from oxidative rearrangement of the steroid backbone. The X-ray crystal structure of the D-homosteroid 3 is provided, and a putative mechanism that invokes a benzilic acid rearrangement for formation of 3 is presented.

引用

页码：2833 / 2836

页数：4

共 5 条

[1]

BHUSHAN V, 1984, SYNTHESIS-STUTTGART, P431

[2] HYDROXYLATION OF PREGN-16-EN-20-ONES .1. PERMANGANATE OXIDATION OF PREGN-16-EN-20-ONES [J].