Heptafluoro-p-tolyl as a selective protecting group for the enone function of androst-4-ene-3, 17-dione: application to the preparation of deuterium-labelled …

M Jarman, R McCague

Index: Jarman, Michael; McCague, Raymond Journal of the Chemical Society, Chemical Communications, 1986 , # 8 p. 635 - 636

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Citation Number: 1

Abstract

Octafluorotoluene reacts with the enone function of andro~t-4-ene-3~17-dione in the presence of caesium fluoride to give specifically a 3,5-dienol ether which has been used to prepare deuterium-labelled testosterone. ... We have recently demonstrated the use of heptafluoro-p-tolyl for the selective protection of phenolic and alcoholic func- tionsl and applications in the synthesis of analogues of the anti-cancer drug tamoxifen.2.3 The phase transfer ...