ISSN:
0170-2041
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Trimethoxyphenyl Compounds, IX. - Boron Heterocycles in Preparative Natural Products Chemistry: A Simple Synthesis of Aurentiacin2,4,6-Trimethoxytoluene, C6H5-X-CO2H (X = CH=CH, CH2-CH2), and boron trifluoride reacted, by selective demethylation, to give crystalline boron heterocycles and, by subsequent hydrolysis, aurentiacin (3b) and dihydroaurentiacin (3c). 2-Phenylpropionic acid acylated 4-hydroxy-2,6-dimethoxytoluene without demethylation. Under more vigorous conditions, diacylation occurred which was accompanied by demethylation. The second acyl group was easily lost.
Notes:
2,4,6-Trimethoxytoluol ergab mit C6H5-X-CO2H (X = CH = CH, CH2-CH2) und Bortrifluorid unter selektiver Entmethylierung kristalline Borheterocyclen. Deren Hydrolyse lieferte Aurentiacin (3b) und Dihydroaurentiacin (3c). 4-Hydroxy-2,6-dimethoxytoluol nahm einen (2-Phenylpropionyl)-Rest ohne, unter verschärften Bedingungen einen zweiten mit gleichzeitiger Entmethylierung auf. Der zweite Acylrest wurde leicht wieder abgespalten.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198219820810
