Total synthesis of 14β-hydroxy-4,9(11)- androstadiene-3,17-dione

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Abstract
The title compound 8, a potential intermediate in the total synthesis of cardiac-active principles and other polyfunctional steroids, is prepared in nine steps using methyl vinyl ketone and 2-methylcyclohexane-1,3-dione as starting materials and acetylene and 2-methylcyclopentane-1,3-dione as additional sources of carbon atoms. In a crucial aldol condensation leading to the closure of steroid ring C, an efficient asymmetric induction by one chiral center leads to the establishment of three new chiral centers.

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