Oxidative β-fragmentation of 19-nor-5α-androstane-3β, 5, 17β-triol 3, 17-diacetate

L Lorenc, L Bondarenko, M Rajković, A Milovanović…

Index: Lorenc, Ljubinka; Bondarenko, Lidija; Rajkovic, Milica; Milovanovic, Aleksandar; Mihailovic, Lj. Mihailo Tetrahedron, 1983 , vol. 39, # 21 p. 3609 - 3614

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Citation Number: 9

Abstract

The preparation of 19-nor-5α-androstane 3β, 5, 17β-triol 3, 17 diacetate (10) is described. When this alcohol was treated with the mercuric oxide-iodine reagent it underwent fragmentation of the C (5)–C (10) bond with formation of a new type of 10-membered ring containing 5, 10-seco-steroidal compounds, ie (Z)-and (E)-19-nor-3β, 17β diacetoxy-5, 10- seco-androst-1 (10)-en-5-one (11 and 12), in 27 and 49% yield, respectively.