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

DOI: 10.1021/jo00193a051

Source and publish data:

Journal of Organic Chemistry p. 3671 - 3672 (1984)

Update date:2022-08-04

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Authors:

Marino, Joseph P.

Dax, Scott L.

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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.

Full text of DOI:10.1021/jo00193a051

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