Asimple synthesis of the saponin OSW-1 aglycone is described.Akey step of the synthesis is the reaction of a recently reported steroidal 17_-hydroxy-22,16-lactone with isoamyllithium. The relative reactivity of the hydroxy groups in the 16_-, 17_-, and 22-positions was examined.
Four ether analogues of OSW-1 aglycone were obtained by alkylation of a steroid alcohol with alkyl bromide. During theWilliamson reaction promoted by sodium hydride in addition to alkylation, an unusual dehydrogenation of secondary alcohol was observed.
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