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Abstract
Abstract A representative cardenolide 1 was synthesized starting from 17-oxo-14α-H androstane derivative 2 , with the introduction of the hydroxy group into the position 14 prior to construction of the butenolide ring. Key steps of the synthesis involve: (1) hydroxylation of 15-ene-17-one 4 in the 14β-position with SeO 2 , (2) oxidative, intramolecular cyclopropane ring formation in malo- nate 7 , (3) regio- and stereoselective opening of the cyclopropane ring in 8 with thiophenolate anion, and (4) acid- catalyzed transformation of acetal 13 into hydroxy aldehyde 14 .
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