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DOI: 10.1055/s-0028-1087294
Synthesis of Cannabinoids
Contributor(s):Philip Kocienski, Indu DagerNorth Carolina State University, Raleigh, USA
A Cyclotrimerization Route to Cannabinoids
Org. Lett. 2008, 10: 2195-2198
Publication History
Publication Date:
20 November 2008 (online)
Key words
cannabinoids - Vollhardt [2+2+2] cyclotrimerization - Colvin rearrangement
Significance
The psychotropic, antiemetic, analgesic, and anticonvulsant properties of Cannabis plants have been known since the third millennium BC. Cannabinoids target two cell receptors: the central cannabinoid receptor CB1 and the peripheral cannabinoid receptor CB2. A [2+2+2] cyclotrimerization reaction gave access to three different cannabinoid analogues from the same intermediate, providing a flexible synthetic route.
Comment
A was prepared from commercially available olivetol in three steps. Different diynes were subjected to the cyclotrimerization reaction conditions and it was found that (1) the C-13 ester analogues of diynes of type D were more regioselective but less reactive and (2) the presence of a bulky group on the alkynes was necessary to achieve high regioselectivity.