𝔖 Bobbio Scriptorium
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The synthesis of deuterium, carbon-14, and carrier-free tritium labeled cannabinoids

✍ Scribed by C. G. Pitt; D. T. Hobbs; H. Schran; C. E. Twine Jr; D. L. Williams

Book ID
102900820
Publisher
John Wiley and Sons
Year
1975
Tongue
French
Weight
940 KB
Volume
11
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

1′,2′‐Dehydroolivetol and its monomethyl ether, 5′‐bromoolivetol, and olivetol‐5,‐^2^H~3~, have been synthesized. Acid catalyzed condensation of the latter three compounds with p‐mentha‐2,8‐dien‐1‐ol gave 1′,2′‐dehydro‐Δ^8^‐THC methyl ether, 5′‐bromo‐Δ^8^‐THC, and Δ^9^‐THC‐5′‐^2^H~3~, respectively. 5′‐Bromo‐Δ^8^‐THC served as a precursor of 4′,5′‐dehydro‐Δ^8^‐ and Δ^8^‐THC, 4′‐ and 5′‐hydroxy‐Δ^8^‐THC, 5′‐dimethylamino‐Δ^8^‐THC and 5′‐carboxy‐Δ^8^‐THC. Reduction of 4′,5′‐dehydro‐Δ^8^‐ and Δ^9^‐THC in the presence of homogeneous catalysts afforded tritium labeled Δ^8^‐THC (50 Ci/mmole) and Δ^9^‐THC (58 Ci/mmole), respectively. Syntheses of Δ^9^‐THC‐11‐^2^H^3^, Δ^9^‐THC‐11‐^14^C cannabinol‐5,‐^2^H~3~′ and other labeled cannabinoids are described.

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