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Synthese de Δ^8^ et Δ^9^ ‐ tetrahydrocannabinol deuteries et trities by Henri Hoellinger; Nguyen-Hoang Nam; Jean-François Decauchereux; Louis Pichat is a Chemistry article available to read on EtoBox.

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## Abstract Cross‐coupling of 3,5‐dimethoxybenzyl bromide and 4‐buten‐magnesium bromide in presence of Li~2~CuCl~4~ afforded 1‐(3,5‐dimethoxyphenyl)‐4pentene. Demethylation of the latter by methylmagnesium iodide in xylene gave rise to 4′,5′‐dehydro‐olivetol. The latter, condensed with trans‐p‐mentha‐2,8‐dien‐1‐ol in the presence of either boron trifluoride etherate or p‐toluenesulfonic acid, gave 4′,5′‐dehydro‐Δ^9^‐ and Δ^8^‐THC respectively. 4′,5′‐dehydro‐Δ^8^‐THC was also obtained by isomerization of 4′,5′‐dehydro‐Δ^9^‐THC. Catalytic selective reduction of these precursors with deuterium or tritium, in the presence of tris(triphenylphosphine)rhodium chloride, afforded Δ^9^‐THC‐4′,5′,‐^2^H or Δ^9^‐THC‐4′,5′‐^3^H (50 Ci/mMole) and Δ^8^‐THC‐4′,5′‐^2^H or Δ^8^‐THC‐4′,5′‐^3^H (56 Ci/mMole).

Who reads Synthese de Δ^8^ et Δ^9^ ‐ tetrahydrocannabinol deuteries et trities?

Author

Henri Hoellinger; Nguyen-Hoang Nam; Jean-François Decauchereux; Louis Pichat

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Inc.; Wiley (ISSN 0022-2135)

Published

1977

Language

EN

Field

Chemistry (Life Sciences)