Enantioselective organocatalytic synthesis of bicyclic resorcinols via an intramolecular Friedel-Crafts-type 1,4-addition: access to cannabidiol analoguesBryant, L. A., Shankland, K. ORCID: https://orcid.org/0000-0001-6566-0155, Straker, H. E., Johnston, C. D., Lees, N. R. and Cobb, A. J.A. (2021) Enantioselective organocatalytic synthesis of bicyclic resorcinols via an intramolecular Friedel-Crafts-type 1,4-addition: access to cannabidiol analogues. Advanced Synthesis and Catalysis, 363 (16). pp. 4067-4074. ISSN 1615-4169
It is advisable to refer to the publisher's version if you intend to cite from this work. See Guidance on citing. To link to this item DOI: 10.1002/adsc.202100647 Abstract/SummaryThe organocatalytic transformation of resorcinols is extremely rare. In this article, we report a highly enantioselective, organocatalytic intramolecular cyclization of these systems by a Friedel–Crafts-type 1,4-addition using a Jørgensen-Hayashi-like organocatalyst with a large silyl protecting group, and show that heat improves reaction yield with virtually no detriment to enantioselectivity. A variety of bicyclic resorcinols were obtained with excellent enantioselectivities (up to 94%). To show the utility of these constructs, and as part of a wider project involving the synthesis of cannabinoid-like compounds, the resorcinol formed was used to generate both ‘normal’ and ‘abnormal’ cannabidiol (CBD) derivatives which were shown to have anticonvulsant activity.
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