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Total Synthesis of (+)‐Rubriflordilactone A
Author(s) -
Goh Shermin S.,
Chaubet Guilhem,
Gockel Birgit,
Cordonnier MarieCaroline A.,
Baars Hannah,
Phillips Andrew W.,
Anderson Edward A.
Publication year - 2015
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.201506366
Subject(s) - total synthesis , enantioselective synthesis , ring (chemistry) , natural product , palladium , component (thermodynamics) , combinatorial chemistry , chemistry , stereochemistry , computer science , organic chemistry , catalysis , physics , thermodynamics
Two enantioselective total syntheses of the nortriterpenoid natural product rubriflordilactone A are described, which use palladium‐ or cobalt‐catalyzed cyclizations to form the CDE rings, and converge on a late‐stage synthetic intermediate. These key processes are set up through the convergent coupling of a common diyne component with appropriate AB‐ring aldehydes, a strategy that sets the stage for the synthetic exploration of other members of this family of natural products.