Synthesis of Oogoniol

Article abstract of DOI:10.1021/jo00262a013

Oogoniol <(24R)-3β,11α,15β,29-tetrahydroxystigmast-5-en-7-one>, a female-activating hormone of Achlya, has been synthesized from 4-androstene-3,11,17-trione.A novel step involved 1,4-addition of the magnesium cyanocuprate derivative of (S)-3-(1-methylethyl)-5-<(tert-butyldimethylsilyl)oxy>pentyl bromide to 3β-hydroxy-15β,16β-epoxy-11-oxo-(17(20)E)-pregna-5,17(20)-diene 3-tert-butyldimethylsilyl ether.Selective hydrogenation of the resulting Δ¹⁶ double bond gave only the stigmastene product with the correct stereochemistry at C₁₅, C₁₇, and C₂₀.