Synthesis of cannabinoids

Details Synthesis of cannabinoids Synthesis of cannabinoids

2007-03-06

2007-03-06

Saeed, Kamal (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S385000, C549S388000

Reexamination Certificate

active

10479021

ABSTRACT:
The present invention relates to a process for the production of compound (A) comprising reacting compound (B) with compound (C). A further ring closure reaction may be necessary. The invention further relates to certain novel compounds of formula (B).

REFERENCES:
patent: 5227537 (1993-07-01), Stoss et al.
patent: 0 494 665 (1992-07-01), None
Handrick et al., Hashish: Synthesis of (-)-Δ9-tetrahydrocannabinol (THC) and its biologically potent metabolite 3′-hydroxy- Δ9-THC, Tetrahedron Lett., No. 8, pp. 681-684 (1979).
Raj K. Razdan, “The Total Synthesis of Cannabinoids” inThe Total Synthesis of Natural Products, vol. 4, ed. John ApSimon (Wiley, Apr. 1981), pp. 239-243.
Leslie Crombie, W. Mary L. Crombie, Sally V. Jamieson, and Christopher J. Palmer, “Acid-catalysed Terpenylations of Olivetol in the Synthesis of Cannabinoids,”J. Chem. Soc. Perkin Trans I, Issue 5, 1998, pp. 1243-1250.
R. W. Rickards, H. Roenneberg, “Synthesis of (−)-Δ9-6a, 10a-tetrahydrocannabinol. Boron trifluoride catalyzed arylation by a homocuprate,”J. Org. Chem.,vol. 49, No. 3, 1984, pp. 572-573.
Wayne E. Childers, Jr. and Harold W. Pinnick, “A Novel Approach to the Synthesis of Cannabinoids,”J. Org. Chem.,vol. 49, No. 26, 1984, pp. 5276-5277.
Tetsuji Kametani, Hiroshi Kurobe, and Hideo Nemoto, Stereoselective Cyclization assisted by the Selenyl Group. Biogenetic-type Synthesis of the p-Methane Series,J. Chem. Soc. Perkin Trans. I, Issue 3, 1981, pp. 756-760.
G .R. Handrick, D. B. Uliss, H. C. Dalzell and R. K. Razdan, Hashish1: Synthesis of (-)-Δ9-Tetrahydrocannabinol (THC) and its Biologically Potent Metabolite 3′-Hydroxy-Δ9-THC,Tetrahedron Letters, No. 8, pp. 681-684.
Leslie Crombie, W. Mary L. Crombie, Christopher J. Palmer and Sally V. Jamieson, “Tetrahydrocannabinols by Terpenylation of Olivetol with (+)-trans-2- and -3-Carene Epoxides,”Tetrahedron Letters, vol. 24, No. 30, 1983, pp. 3129-3132.
International Search Report dated Sep. 9, 2002, from International Application No. PCT/GB02/02159.
British Search Report dated Nov. 27, 2001, from British Application No. 0112752.1.

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