STUDIES ON THE CONSTRUCTION OF THE 2-ISOOCTYL SIDE-CHAIN IN 17-AZASTEROIDS

Authors
MORZYCKI JW LOTOWSKI Z
Citation
Jw. Morzycki et Z. Lotowski, STUDIES ON THE CONSTRUCTION OF THE 2-ISOOCTYL SIDE-CHAIN IN 17-AZASTEROIDS, Monatshefte fuer Chemie, 126(1), 1995, pp. 119-128
Citations number
12
Categorie Soggetti
Chemistry
Journal title
Monatshefte fuer Chemie → ACNP
ISSN journal
00269247
Volume
126
Issue
1
Year of publication
1995
Pages
119 - 128
Database
ISI
SICI code
0026-9247(1995)126:1<119:SOTCOT>2.0.ZU;2-1
Abstract
The transformations of (20R)- and (20S)-3 hydroxy-16-oxo-24-nor-17-aza chol-5-eno-23-nitriles towards the 17-aza analogue of cholesterol are described. Attempts of a direct addition of a four carbon atom fragmen t to nitriles were unsuccessful. Alternately, nitriles were transforme d via carboxylic acids, methyl esters and primary alcohols into iodide s. The coupling reaction of(20S)-iodide with (i-Bu)(2)CuLi afforded th e desired product in low yield but failed in the case of the 20R epime r.