A New Method of Cyclodehydration of 3,3-Dialkyl-1-Oxo-1-(2- hydroxyaryl)propan-3-ols to 2,2-Dialkyl-4-chromanones: Synthesis of Cannabinoid Synthon

1 January 1989

journal article
research article
Published by Taylor & Francis in Synthetic Communications

Vol. 19 (1-2) , 159-166
https://doi.org/10.1080/00397918908050965

Abstract

A new method for cyclodehydration of o-hydroxyaryl-β-ketols to 4-chromanones using HMPT is described. The method has general applicability. It is particularly useful for the cyclisation of labile intermediates as exemplified by the synthesis of cannabinoid synthon, 2-methyl-2-(4-methyl-3-pentenyl)-7-methoxy-4-chromanone.

Keywords

This publication has 2 references indexed in Scilit:

Enolates of o-hydroxyacetophenones: novel synthesis of 2,2-dialkyl-4-chromanones
Tetrahedron Letters, 1979
A carbonium ion mechanism for the dehydration of alcohols in hexamethylphosphoric triamide : comparison with p-nitrobenzoate pyrolysis.
Tetrahedron Letters, 1972