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Synthesis 1991; 1991(10): 851-853
DOI: 10.1055/s-1991-26590
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Studies on the Synthesis of (-)-11-Nor-9-carboxy-Δ9-Tetrahydrocannabinol (THC) and Related Compounds: An Improved Oxidative Procedure

Craig Siegel* , Patrick M. Gordon, Raj K. Razdan
  • *Organix, Inc., 65 Cummings Park, Woburn, MA 01801-2105, USA
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Publication Date:
29 April 2002 (online)

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A facile procedure is described whereby Δ9-THC aldehydes 4, as their tert-butyldimethylsilyl derivatives, are conveniently oxidized to the corresponding acids with sodium chlorite in the presence of a large excess of 2-methyl-2-butene without isomerization of the Δ9-double bond. Deprotection of the O-protecting group with tetrabutylammonium fluoride in tetrahydrofuran gave the acids 2 in an overall yield of ≥ 80%. A study of other oxidizing agents and protecting groups demonstrated that this is the procedure of choice for the preparation of 9-carboxy-Δ9-tetrahydrocannabinols.