Synthesis and X-ray Crystal Structure of 3-oxo-23, 24-Dinorchol-4-Ene-22-Cyanohydrin

Abstract

22R) and (22S) 3-Oxo-23,24-dinorchol-4-ene-22-cyanohydrin have been synthesised from 3-oxo-23,24-dinorchol-4ene-22-al and the crystal structure of the (22R) epimer has been determined by X-ray crystallography.

Synthesis of hydroxy acids of dinorcholane and 5β-cholane

“…Nuclear magnetic resonance (NMR) spectra were recorded on a Varian Unity INOVA 400 MHz NMR spectrometer. NMR spectra were obtained in CDCl 3 . Chemical shifts (d) are reported in ppm downfield from TMS, using the residual solvent peak (7.25 ppm for 1 H and 77.23 ppm for 13 C) as an internal standard and coupling constants (J) in Hz.…”

“…However, if a chiral centre already exists next to the carbonyl carbon, two possible diastereomeric products are formed, and they are not of equal amounts. As part of our on-going studies on the synthesis and reactions of steroid monomers and dimers, [2][3][4][5][6][7][8] we now report on the development of a convenient and general method for the synthesis of diasteriomerc (55:45) dinorcholane hydroxy acids and 5β-cholane hydroxy acid using readily available dinorcholanal and 5β-cholane-3α,24-diol as the starting materials.…”

X-ray crystal structure of 3β,22-dihydroxy-23,24-dinorchol-4-ene

“…2 Previously, the helical arrangement of steroid molecules in the solid state formed by a combination of the crystallographic screw axis and intermolecular hydrogen bonding has been reported . 3…”