The Synthesis of 2α,3α-Isopropylidenedioxy-6,6-Ethylenedioxy-5α-Androst-15-En-17-One and Its 2β,3β-Isomer

R. P. Litvinovskaya^1 #, A. V. Baranovsky¹, M. A. Averkova¹ and V. A. Khripach¹

^#Fax: (375-17) 267-86-47; e-mail: litvin@iboch.bas-net.by

¹Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Kuprevicha 5/2, Minsk, 220141, Belarus

Received: June  22, 2006;  in final form: December  19, 2006

Abstract.  Androstane and Δ¹⁵-androstane analogues of brassinosteroids were synthesized from dehydroepiandrosterone. The key stage, hydroxylation of 17β-acetoxyandrost-2-en-6-one double bond with OsO₄, yielded the corresponding 2α,3α- and 2β,3β-diols. The target 2α,3α-isopropylidenedioxy-6,6-ethylenedioxy-5α-androst-15-en-17-one and its 2β,3β-isomer were obtained by dehydrosilylation of the corresponding silylenol ethers with palladium acetate.

Key words:  androstane and Δ¹⁵-androstane analogues, brassinosteroids - synthesis

Russian Journal of Bioorganic Chemistry 2007, 33 (3): 320-325