An Efficient Desilylation Method for the Generation of o-Quinone Methides: Application to the Synthesis of (+)- and (-)-Hexahydrocannabinol

Article abstract of DOI:10.1021/jo00193a051

The bis-silylated o-hydroxybenzyl alcohol derivative 1 undergoes regiospecific 1,4-desilylation-elimination to an incipient o-quinone methide that is trapped in an intramolecular Diels-Alder reaction to yield (+)- or (-)-hexahydrocannabinols.