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Paper | Regular issue | Vol 34, No. 6, 1992, pp.1107-1117
Published online, 1st January, 1970
DOI: 10.3987/COM-92-5971
A Facile Synthesis of 9-Nor-9-hydroxyhexahydrocannabinol via Intramolecular Reverse Electron Demand Diels-Alder Cyclization

Zhan Guo Lu and Seiichi Inoue*

*Department of Synthetic Chemistry, Faculty of Engineering, Yokohama National University, Tokiwadai, Hodogaya-ku, Yokohama 240, Japan


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).