Journal of the American Chemical Society

α-Iodoketones (Part 3). 1 Synthesis of 21-Iodo-Δ16-20-keto Steroids by the N-Iodosuccinimide-Enol Acetate Reaction2

C Djerassi, CT Lenk

Index: Djerassi; Lenk Journal of the American Chemical Society, 1954 , vol. 76, p. 1722,1725

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Citation Number: 14

Abstract

Unsaturated enol acetates such as 20-a~ etoxy-A1~**~-dienes, readily obtainable by the reaction of A16-20-keto steroids with isopropenyl acetate, are convertible in excellent yield to the hitherto inaccessible 21-i0do-A~~-20-ketosteroids by treatment with N- iodosuccinimide in dioxane solution. Replacement of the halogen atom by acetate proceeds in nearly quantitative yield, thus opening a route to the A16-20-keto-21-acetates and ...