Synthesis of 15?-hydroxyalkyl-substituted (17Z)-pregn-17-enes, their ethers and esters

Abstract

Proceeding from D 15 -17-ketosteroids via copper(I)-catalyzed 1,4-addition of Grignard reagent followed by modification of the 15-alkenyl substituent, introduction of a 17-ethylidene component via Wittig reaction, and transformations in the A and B rings of the steroid molecule we obtained a series of 15b-hydroxyalkyl-substituted (17Z)-pregn-17-enes, their ethers and esters.

Palladium-Catalyzed Saegusa–Ito Oxidation: Synthesis of α,β-Unsaturated Carbonyl Compounds from Trimethylsilyl Enol Ethers

“…: 110−112 °C (hexane)). 47 All spectroscopic data were identical to those previously reported. 47 3a-Vinyl-2,3,3a,4,5,6-hexahydroinden-1-one (2h).…”

NMR spectra of androstane analogs of brassinosteroids

“…Discussion of Results. Analysis of 1 H NMR spectra. The proton signals in the spectra were assigned using 2D HSQC and COSY NMR spectroscopy techniques.…”