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Synthesis 1994; 1994(5): 486-488
DOI: 10.1055/s-1994-25509
short paper
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Synthesis of (R)- and (S)-4′-Acetoxyolivetol [(R)- and (S)-5-(4′-Acetoxypentyl)-1, 3-benzenediol]: Key Intermediates in the Synthesis of Tetrahydrocannabinol Derivatives

M. Singer* , C. Siegel, P. M. Gordon, A. K. Dutta, R. K. Razdan
  • *Organix Inc., 65 Cummings Park, Woburn, Massachusetts 01801 USA
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Publication Date:
17 September 2002 (online)

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The synthesis of (R)- and (S)-4′-acetoxyolivetols, key intermediates in the synthesis of tetrahydrocannabinol derivatives from 3,5-dihydroxybenzoic acid (4) is described. The 3,5-dihydroxy groups were protected as their tert-butyldimethylsilyl derivatives, and the benzoic acid group was transformed into the benzyl-1,3-dithiane derivative 8. Treatment of the anion of 8 with the chiral 1,2-epoxypropane gave the dithianyl alcohol 9, which after acetylation followed by desulfurization and deprotection of the phenolic hydroxyl groups, furnished the desired 4′-acetoxyolivetols (2a,b) in an overall yield of 13 %.