Diacetoxyiodobenzene-mediated synthesis of unnatural furospirostane sapogenins derived from diosgenin and tigogenin.

Jacqueline Sánchez-Flores, Margarita Romero-Ávila, Anielka Rosado-Abón, Marcos Flores-Álamo, Martín A Iglesias-Arteaga

Index: Steroids 78(9) , 798-802, (2013)

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Abstract

Two unnatural steroid sapogenins bearing a furospirostane side chain were prepared starting from the readily available spirostane sapogenins, tigogenin and diosgenin following a synthetic protocol that included: (i) introduction of a carbonyl group at position C-23, (ii) diacetoxyiodobenzene-induced F-ring contraction and (iii) LiAlH4 reduction of the newly emerged methoxycarbonyl moiety. The structures of the new compounds were corroborated by NMR and X-ray studies. Copyright © 2013 Elsevier Ltd. All rights reserved.