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Highly Enantioselective, Organocatalytic, and Scalable Synthesis of a Rare cis,cis ‐Tricyclic Diterpenoid
Author(s) -
Townsend Daniel,
Shankland Kenneth,
WeymouthWilson Alex,
Komsta Zofia,
Evans Tim,
Cobb Alexander J. A.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202000164
Subject(s) - enantioselective synthesis , tricyclic , decalin , organocatalysis , chemistry , stereochemistry , flexibility (engineering) , combinatorial chemistry , terpenoid , catalysis , organic chemistry , mathematics , statistics
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.