The synthesis of 2alpha,3alpha-isopropylidenedioxy-6,6-ethylenedioxy-5alpha-androst-15-en-17-one and its 2beta,3beta-isomer
Litvinovskaia, R.P.; Baranovskiĭ, A.V.; Aver'kova, M.A.; Khripach, V.A.
Bioorganicheskaia Khimiia 33(3): 342-348
2007
ISSN/ISBN: 0132-3423 PMID: 17682391 Document Number: 605460
Androstane and delta15-androstane analogues of brassinosteroids were synthesized from dehydroepiandrosterone. The key stage, hydroxylation of 17beta-acetoxyandrost-2-en-6-one double bond with OsO4, yielded the corresponding 2alpha,3alpha- and 2beta,3beta-diols. The target 2alpha,3alpha-isopropylidenedioxy-6,6-ethylenedioxy-5alpha-androst-15-en-17-one and its 2beta,3beta-isomer were obtained by dehydrosilylation of the corresponding silylene ethers with palladium acetate.
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