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Bryant LA, Shankland K, Straker HE, et al. Enantioselective Organocatalytic Synthesis of Bicyclic Resorcinols . Adv Synth Catal. 2021;363(16):4067-4074doi: 10.1002/adsc.202100647.
Bryant, L. A., Shankland, K., Straker, H. E., Johnston, C. D., Lees, N. R., & Cobb, A. J. A. (2021). Enantioselective Organocatalytic Synthesis of Bicyclic Resorcinols . Advanced synthesis & catalysis, 363(16), 4067-4074. https://doi.org/10.1002/adsc.202100647
Bryant, Laura A, et al. "Enantioselective Organocatalytic Synthesis of Bicyclic Resorcinols ." Advanced synthesis & catalysis vol. 363,16 (2021): 4067-4074. doi: https://doi.org/10.1002/adsc.202100647
Bryant LA, Shankland K, Straker HE, Johnston CD, Lees NR, Cobb AJA. Enantioselective Organocatalytic Synthesis of Bicyclic Resorcinols . Adv Synth Catal. 2021 Aug 13;363(16):4067-4074. doi: 10.1002/adsc.202100647. Epub 2021 Jul 12. PMID: 34594164; PMCID: PMC8457227.
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Adv Synth Catal. 2021 Aug 13;363(16):4067-4074. doi: 10.1002/adsc.202100647. Epub 2021 Jul 12.

Enantioselective Organocatalytic Synthesis of Bicyclic Resorcinols .

Advanced synthesis & catalysis

Laura A Bryant, Kenneth Shankland, Hannah E Straker, Callum D Johnston, Nicholas R Lees, Alexander J A Cobb

Affiliations

  1. Department of Chemistry King's College London 7 Trinity Street London SE1 1DB UK.
  2. School of Chemistry Food and Pharmacy (SCFP) University of Reading Whiteknights Reading, Berks RG6 6AD UK.
  3. GW Pharmaceuticals Kent Science Park Sittingbourne Kent ME9 8AG UK.

PMID: 34594164 PMCID: PMC8457227 DOI: 10.1002/adsc.202100647

Abstract

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.

© 2021 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH.

Keywords: Michael addition; cannabinoids; organocatalysis; resorcinols

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