A new stereocontrolled entry into the anthracyclinone families. Part 1: Synthesis of bicyclic precursors of 4-demethoxy-7-deoxy-derivatives

A new and versatile strategy to obtain enantiomerically pure bicyclic precursors of compounds belonging to different anthracyclinone families is reported. Completely stereoselective hydrocyanation of ( R)-4-(2,5-dimethoxyphenyl)-1- p-tolylsulfinyl-2-butanone and further intramolecular capture of the...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron: asymmetry 1999-07, Vol.10 (15), p.2935-2944
Main Authors: Garcı́a Ruano, José L., Garcı́a Paredes, Cristina, Hamdouchi, Chafiq
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A new and versatile strategy to obtain enantiomerically pure bicyclic precursors of compounds belonging to different anthracyclinone families is reported. Completely stereoselective hydrocyanation of ( R)-4-(2,5-dimethoxyphenyl)-1- p-tolylsulfinyl-2-butanone and further intramolecular capture of the Pummerer intermediate generated from the resulting sulfinylcyanohydrin are the key steps to obtain the bicyclic nitrile 2 with the proper configuration and functionality at C-9.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(99)00280-3