Premium
Synthese de Δ 8 et Δ 9 ‐ tetrahydrocannabinol deuteries et trities
Author(s) -
Hoellinger Henri,
Nam NguyenHoang,
Decauchereux JeanFrançois,
Pichat Louis
Publication year - 1977
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580130316
Subject(s) - chemistry , bromide , medicinal chemistry , iodide , boron trifluoride , isomerization , triphenylphosphine , methyl iodide , catalysis , radiochemistry , nuclear chemistry , organic chemistry
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).