Synthesis of anthracyclinones. Part 1. Regioselective alkylation of 5-hydroxyquinizarin
- 1 October 1984
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 62 (10) , 1922-1925
- https://doi.org/10.1139/v84-329
Abstract
Condensation of leuco-5-hydroxyquinizarin with aldehydes under Marschalk conditions (sodium hydroxide – water) gives 2-alkyl-5-hydroxyquinizarins with high regioselectivity, while the 3-alkyl compounds are obtained under Lewis conditions (piperidinium acetate – isopropanol). Reaction of the quinone with nitronate anions in methanol yields 2-alkyl derivatives exclusively.This publication has 2 references indexed in Scilit:
- Anthracyclinones. Part 1. A versatile synthesis of the anthracyclinone system using a chiral template derived from a carbohydrateJournal of the Chemical Society, Perkin Transactions 1, 1983
- Stereoselektive Totalsynthese von AnthracyclinonenEuropean Journal of Inorganic Chemistry, 1978