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9‐Membered Carbocycle Formation: Development of Distinct Friedel–Crafts Cyclizations and Application to a Scalable Total Synthesis of (±)‐Caraphenol A
Author(s) -
Wright Nathan E.,
Snyder Scott A.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201311299
Subject(s) - trimer , total synthesis , ring (chemistry) , yield (engineering) , chemistry , friedel–crafts reaction , aryl , stereochemistry , combinatorial chemistry , catalysis , organic chemistry , materials science , dimer , alkyl , metallurgy
Explorations into a series of different approaches for 9‐membered carbocycle formation have afforded the first reported example of a 9‐ exo ‐dig ring closure via a Au III ‐promoted reaction between an alkyne and an aryl ring as well as several additional, unique Friedel–Crafts‐type cyclizations. Analyses of the factors leading to the success of these transformations are provided, with the application of one of the developed 9‐membered ring closures affording an efficient and scalable synthesis of the bioactive resveratrol trimer caraphenol A. That synthesis proceeded with an average yield of 89 % per step (7.8 % overall yield) and has provided access to more than 600 mg of the target molecule.