Carbonyl to methylene conversions at the tricarbonyl-portion of ascomycin derivatives

Treatment of ascomycin or its O-TBDMS-derivatives with hydrogen sulfide and pyridine in dimethylformamide solution results in deoxygenation reactions at the tricarbonyl sequence of the binding domain. 9-deoxo-ascomycins ( 5a-c) are obtained in high yields (75–85%) together with small amounts (2–14%...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 1999-10, Vol.40 (44), p.7761-7764
Main Authors: Baumann, Karl, Knapp, H, Strnadt, G, Schulz, G, Grassberger, M.A
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:Treatment of ascomycin or its O-TBDMS-derivatives with hydrogen sulfide and pyridine in dimethylformamide solution results in deoxygenation reactions at the tricarbonyl sequence of the binding domain. 9-deoxo-ascomycins ( 5a-c) are obtained in high yields (75–85%) together with small amounts (2–14% yield) of 10-deoxo-ascomycins ( 6a-c). The novel derivative 10-deoxo-ascomycin ( 6a) is accessible in excellent yield (85%) from the 10-amino-analog of ascomycin upon reaction with hydrogen sulfide in the absence of base. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)01622-6