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Synfacts 2006(9): 0927-0927  
DOI: 10.1055/s-2006-949240
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Cannabidiols via Alkenylation of Cyclohexenyl Monoacetate

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
Y. Kobayashi*, A. Takeuchi, Y.-G. Wang
Tokyo Institute of Technology, Yokohama, Japan
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

Various propenyl nucleophiles were tested for the nucleophilic displacement of an AcO group in the synthesis of cannabidiols. These compounds have attracted attention as non-psychotropic drugs (related to Δ9-tetrahydrocanna­binol). The use of zinc reagent 1 was found to be superior to Mg and various vinyl boron derivatives. The reaction proceeded under NiCl2(tpp)2 catalysis with TMEDA additive and gave the desired regioisomer with 94:6 selectivity.