114028-39-6Relevant articles and documents
A concise methodology for the synthesis of (-)-Δ9-tetrahydrocannabinol and (-)-Δ9-tetrahydrocannabivarin metabolites and their regiospecifically deuterated analogs
Nikas, Spyros P.,Thakur, Ganesh A.,Parrish, Damon,Alapafuja, Shakiru O.,Huestis, Marilyn A.,Makriyannis, Alexandros
, p. 8112 - 8123 (2008/02/08)
The availability of tetrahydrocannabinols (Δ9-THC), tetrahydrocannabivarins (Δ9-THCV), and their metabolites in both their undeuterated and deuterated forms is critical for the analysis of biological and toxicological samples. We report here a concise methodology for the syntheses of (-)-Δ9-THC and (-)-Δ9-THCV metabolites in significantly improved overall yields using commercially available starting materials. Our approach allowed us to obtain the key intermediates (6aR,10aR)-9-nor-9-oxo-hexahydrocannabinols in four steps from (+)-(1R)-nopinone. This was followed by an optimized Shapiro reaction to give the (-)-11-nor-9-carboxy-metabolites, which were converted to their respective (-)-11-hydroxy analogs. The synthetic sequence involves a minimum number of steps, avoids undesirable oxidative conditions, and incorporates the costly deuterated resorcinols near the end of the synthetic sequence. This methodology enabled us to synthesize eight regiospecifically deuterated (-)-Δ9-THC and (-)-Δ9-THCV metabolites in a preparative scale and high optical purity without deuterium scrambling or loss.
Preparation of Racemic, (-)- And (+)-11-Nor-δ9-Tetrahydrocannabinol-9-carboxylic Acid
Kachensky, David F.,Hui, Raymond A. H. F.
, p. 7065 - 7068 (2007/10/03)
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A convenient synthesis of (-)-11-nor-Δ9-tetrahydrocannabinol-9-methanol
Tius,Gu,Kerr
, p. 62 - 63 (2007/10/02)
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