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Towards the Total Synthesis of Gedunin: Construction of the Fully Elaborated ABC Ring System
Author(s) -
Pinkerton David M.,
Bernhardt Paul V.,
Savage G. Paul,
Williams Craig M.
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700013
Subject(s) - annulation , chemistry , total synthesis , ring (chemistry) , natural product , combinatorial chemistry , key (lock) , nanotechnology , stereochemistry , organic chemistry , catalysis , computer science , materials science , computer security
The widely occurring tetranortriterpene natural product gedunin has a well‐established range of important biological properties. Although this molecule has received substantial semi‐synthetic attention from medicinal chemists, it has not received devoted de novo synthetic attention since it was first isolated in 1960. A key feature of the approach presented herein was the decision to utilize a Robinson annulation reaction, which facilitated the installation of the challenging 7‐acetoxy functional group and the completion of the fully functionalized ABC ring system.