The Journal of Organic Chemistry

Photoinduced transformations. 76. A four-step substitution of a carbonyl group of steroidal ketones by an oxygen atom. A new method for the synthesis of cyclic ethers

H Suginome, S Yamada

Index: Suginome, Hiroshi; Yamada, Shinji Journal of Organic Chemistry, 1985 , vol. 50, # 14 p. 2489 - 2494

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Citation Number: 57

Abstract

We set out to describe a new and versatile method for transforming steroidal five-and six- membered cyclic ketones as starting materials into steroidal cyclic ethers with the same ring size via four steps; Baeyer-Villiger oxidation of a steroidal ketone to a lactone followed by ita reduction with DIBAL gives the corresponding lactol. The irradiation of the hypoiodite generated in situ by means of the reaction of the lactol by an excess of mercury (I1) oxide- ...