An improved procedure for the conversion of certain coumarins to 2,2-dimethylchromenes: efficient transformation of umbelliferone to precocene 1
- 1 September 1983
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 61 (9) , 1963-1964
- https://doi.org/10.1139/v83-338
Abstract
An improved method for transforming certain coumarins to 2,2-dimethylchromencs has been developed. Umbelliferone (1b) was efficiently converted to precocene 1 (2b) (73%) by etherification to herniarin (1c) with tetramethylorthocarbonate, followed by reaction with methyllithium and cyclization of the resulting phenolic alcohol on silica gel.This publication has 3 references indexed in Scilit:
- Lethal metabolism of precocene-I to a reactive epoxide by locust corpora allataNature, 1980
- Discovery of Insect Anti-Juvenile Hormones in PlantsScience, 1976
- Syntheses de Chromenes Substitues Synthèse du diméthoxy‐6‐7 diméthyl‐2‐2 Δ‐3 chroméne (agératochroméne)Bulletin des Sociétés Chimiques Belges, 1958