The total synthesis of some tetrahydrocannabinol metabolites

Creator: 

Guiver, Michael Dominic

Date: 

1980

Abstract: 

An efficient synthesis of the metabolite 11-hydroxy-Δ8-tetrahydrocannabinol (2) has been developed, based on the one-carbon homologation of 11-nor-9-ketohexahydrocannabinol (69). The ketone 69 was converted to the intermediate epoxysulphone 77 and cleaved under acid-catalysed conditions using magnesium bromide in ether to give 9β-bromo-11-oxo-hexahydrocannabinol (78b). The metabolite 11-oxo-Δ9-tetrahydrocannabinol (20) was formed as a minor byproduct of this reaction and was reduced to the metabolite 11-hydroxy-Δ9-tetrahydrocannabinol (1).

Attempts to prepare 1 by the intramolecular displacement of bromide by the phenoxide anion in 78b achieved only limited success; under standard dehydrobromination conditions, however, the metabolite 2 was furnished in 64% overall yield.

An alternative route to the metabolite 1, based on the reaction of 69 with the lithium anion of 1,3-dithiane, met with no success; unidentified products were isolated.

Subject: 

Tetrahydrocannabinols

Language: 

English

Publisher: 

Carleton University

Thesis Degree Name: 

Master of Science: 
M.Sc.

Thesis Degree Level: 

Master's

Thesis Degree Discipline: 

Chemistry

Parent Collection: 

Theses and Dissertations

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