1,4-Addition of vinylmagnesium bromide to .ALPHA.,.BETA.-unsaturated steroidal ketones. II. Reaction of 1-En-3-oxo steroids.

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The reaction of 1-en-3-oxo A/B trans steroid with vinylmagnesium bromide in the presence of cupric acetate afforded 1α-vinyl-3-oxo steroid. The configuration of the vinyl group introduced by the reaction was found to be α-oriented by the transformation of II into the lactone (VIII). The stereochemistry of the reduction of 1α-alkyl-3-oxo steroids and 5β-alkyl-3-oxo steroids with complex metal hydride was also studied.

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