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Issue 5, 1988
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Synthesis of bibenzyl cannabinoids, hybrids of two biogenetic series found in Cannabis sativa

Abstract

Syntheses of a series of compounds which merge a m-dihydroxybibenzyl with a terpenoid structure, giving a series of hybrid cannabinoids in which products of two major biogenetic routes of Cannabis are united, are described. The compounds made are the bibenzyl/o- and p-cannabigerols (19) and (18)/o- and p-cannabidiols (21) and (20),/Δ1-THC (22),/Δ6-THC (23),/o- and p-cannabichromenes (25) and (24),/o- and p-cannabicyclols (28) and (27) and/cannabicitran (26). Chromatographic and spectral data are listed in order to facilitate search for such ‘crossed’ types since only the bibenzyl cannabigerols and a chromene have as yet been found in natural sources.

The bibenzyl/p-cannabigerol (18) has been reported in Helichrysum umbraculigerum(Compositae) and the liverwort Radula variabilis. Our synthetic work confirms the former observation, but the liverwort compound appears to be its o-isomer.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1988, 1263-1270
Article type
Paper

Synthesis of bibenzyl cannabinoids, hybrids of two biogenetic series found in Cannabis sativa

L. W. Crombie, W. M. L. Crombie and D. F. Firth, J. Chem. Soc., Perkin Trans. 1, 1988, 1263
DOI: 10.1039/P19880001263

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