Journal of the American Chemical Society

Studies in the Synthesis of Triamcinolone. The Condensation of 16α, 17α-Isopropylidenedioxy-4, 9 (11)-pregnadiene-3, 20-dione with Ethyl Oxalate

GR Allen Jr, MJ Weiss

Index: Allen; Weiss Journal of the American Chemical Society, 1959 , vol. 81, p. 4968,4973

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Citation Number: 11

Abstract

Etlioxalglatiun of 16a, lT~-isopropylidenedioxy-4, 9 ( 1 l)-pregnadiene-3, 23-dione (XI), which was prepared from 16a, 17aepoxy-1 lor-hydroxyprogesterone (11), in the presence of a molar equivalent of sodiurn methoxitie gave exclusively the 2-ethoxalyl derivative XVIII, which was converted by a six-step procedure into 9~-fluoro-ll, 8, 16or, l7a-trihydrosy-1, 4- pregna-diene-3, 20-dione (XXL'II). Bis-ethoxalylation of XI led to the preparation of the 2a, ...