Highly Enantioselective,Organocatalytic, and Scalable Synthesis of a Rare cis,cis-Tricyclic Diterpenoid |
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| Authors: | Daniel Townsend Prof Dr Kenneth Shankland Dr Alex Weymouth-Wilson Dr Zofia Komsta Dr Tim Evans Dr Alexander J A Cobb |
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| Institution: | 1. Department of Chemistry, King's College London, 7 Trinity Street, London, SE1 1DB UK;2. School of Chemistry, Food and Pharmacy, University of Reading, Whiteknights, Reading, Berks, RG6 6AD UK;3. Dextra Laboratories Ltd., Thames Valley Science Park, The Gateway, 1 Collegiate Square, Reading, RG2 9LH UK |
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| Abstract: | 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. |
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| Keywords: | asymmetric synthesis decalin hydrindane organocatalysis terpenes |
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