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

Bryant, L. A., Shankland, K., 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

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To link to this item 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
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
ID Code:100186
Publisher:Wiley

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