Enantioselective organocatalytic synthesis of bicyclic resorcinols via an intramolecular Friedel-Crafts-type 1,4-addition: access to cannabidiol analogues

Bryant, 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 doi: 10.1002/adsc.202100647

Abstract/Summary

The 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.

Item Type	Article
URI	https://reading-clone.eprints-hosting.org/id/eprint/100186
Item Type	Article
Refereed	Yes
Divisions	Interdisciplinary centres and themes > Chemical Analysis Facility (CAF) Interdisciplinary centres and themes > Chemical Analysis Facility (CAF) > Xray (CAF) Life Sciences > School of Chemistry, Food and Pharmacy > School of Pharmacy > Pharmaceutics Research Group
Publisher	Wiley
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