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Asymmetric Total Syntheses of Communesin F and a Putative Member of the Communesin Family
Author(s) -
Park Jisook,
Jean Alexandre,
Chen David Y.K.
Publication year - 2017
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.201707806
Subject(s) - aminal , oxindole , total synthesis , family member , stereochemistry , enantioselective synthesis , chemistry , combinatorial chemistry , biology , catalysis , biochemistry , medicine , family medicine
Here we report asymmetric total syntheses of communesin F and a putative member of the communesin family of bis‐aminal alkaloid natural products. The successful strategy featured the invention of an asymmetric organocatalytic reaction to unify two oxindole subunits, a Ti(O i Pr) 4 ‐mediated dehydrative skeletal rearrangement, and a late‐stage Pd(OAc) 2 ‐catalyzed directed CH‐alkenylation reaction. Collectively, the synthetic technologies disclosed herein enabled the preparation of a late‐stage polycyclic intermediate catered for the synthesis of both naturally occurring and designed communesins. More importantly, speculated and yet to be discovered member(s) of the communesin family can now be accessed to facilitate a better understanding of the communesin biosynthetic network.