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Start Over Author "Zhan-Guo Lu" Journal heterocycles
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1. A Facile Synthesis of 9-Nor-9-hydroxyhexahydrocannabinol via Intramolecular Reverse Electron Demand Diels-Alder Cyclization

Author

Seiichi Inoue and Zhan Guo Lu

Subjects
Pharmacology, Intramolecular reaction, 9-hydroxyhexahydrocannabinol, Chemistry, Organic Chemistry, Ether, Olivetol, Medicinal chemistry, Cycloaddition, Analytical Chemistry, Turn (biochemistry), chemistry.chemical_compound, Intramolecular force, Phenols
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
1992

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