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1. ChemInform Abstract: A Facile Synthesis of 9-Nor-9-hydroxyhexahydrocannabinol via Intramolecular Reverse Electron Demand Diels-Alder Cyclization

Author

Zhan Guo Lu and Seiichi Inoue

Subjects
Turn (biochemistry), chemistry.chemical_compound, chemistry, 9-hydroxyhexahydrocannabinol, Intramolecular force, Diels alder, Organic chemistry, Ether, General Medicine, Olivetol, Medicinal chemistry, Cycloaddition
Abstract

A simple and efficient new synthesis of 9-nor-9-hydroxyhexahydrocannabinol is achieved, through the intramolecular [4+2] cycloaddition of an o-quinonemethide which is generated from 2-(1-hydroxy-3-methoxymethoxy-7-methyl-6-octenyl)-1,3-bis(O-methoxymethyl)olivetol (12b), which in turn is prepared by reaction of the lithiated olivetol bis(methoxymethyl)ether with 3-methoxymethoxy-7-methyl-6-octenal (9)

Published
2010

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