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Highly enantioselective, organocatalytic and scalable synthesis of a rare cis-cis-tricyclic diterpenoid

Townsend, D., Shankland, K., Weymouth-Wilson, A., Komsta, Z., Evans, T. and Cobb, A. (2020) Highly enantioselective, organocatalytic and scalable synthesis of a rare cis-cis-tricyclic diterpenoid. Chemistry- A European Journal, 26 (16). pp. 3504-3508. ISSN 1521-3765

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To link to this item DOI: 10.1002/chem.202000164

Abstract/Summary

A highly enantioselective, organocatalytic and scalable synthesis of a very unusual cis-decalin-cis-hydrindane tricyclic diterpenoid system has been achieved. Despite the prevalent pharmacological space that the related trans-trans and trans-cis-systems occupy, there have been no reports of an asymmetric synthesis of the cis-cis systems in the literature until now. We demonstrate the flexibility of our approach not only through access to a diverse range of products, all of which are attained in exceptionally high selectivities, but also by showing their easy conversion to the corresponding trans-cis-system and other derivatives.

Item Type:Article
Refereed:Yes
Divisions:Interdisciplinary centres and themes > Chemical Analysis Facility (CAF) > Xray (CAF)
Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > School of Pharmacy > Pharmaceutics Research Group
ID Code:88756
Publisher:Wiley

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