Stereoselectivity in the epoxidation and cis-hydroxylation of 16-methylene-estra-1,3,5(10)-trienes

Add time:08/06/2019    Source:sciencedirect.com

Epoxidation of 3-methoxy-16-methylene-estra-1,3,5(10)-trien-17-one in the presence of alkaline hydrogen peroxide gives rise to (16R)- and (16S)-spiro[3-methoxy-17-oxoestra-1,3,5(10)-triene-16,2′-oxirane] in similar proprotions. Epoxidation of the corresponding 16-methylene 17μ-alcohol and 16-methylene-17μ-acetate with m-chloroperbenzoic acid does not display any significant direting effects associated with allylic functionally, whereas Sharpless epoxidation of the 16-methylene 17μ-alcohol is highly stereoselectivity, leading exclusively to the (16R) isomer. cis-Hydroxylation of the 16-methylene 17-ketone with osmium tetroxide/ 4-methylmorpholine-4-oxide proceeds stereoselectively to give mainly 16α-hydroxy-16μ-hydroxymethyl-3-methoxyestra-1,3,5(10)-trien-17-one. The isomeric addition products derived from these reactions are correlated by appropariate interconversions, and the assignments are corroborated by comparative reactivity of derived products.

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