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Concise Total Synthesis of (−)‐Frondosin B Using a Novel Palladium‐Catalyzed Cyclization
Author(s) -
Hughes Chambers C.,
Trauner Dirk
Publication year - 2002
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 - 10.1002/1521-3773(20020503)41:9<1569::aid-anie1569>3.0.co;2-8
Subject(s) - palladium , total synthesis , catalysis , chemistry , metabolite , stereochemistry , inversion (geology) , organic chemistry , biology , biochemistry , paleontology , structural basin
Sidestepping stereochemical inversion : In an expedient, asymmetric total synthesis of (−)‐frondosin B a novel palladium‐catalyzed cyclization establishes the tetracyclic skeleton (see scheme). The absolute stereochemistry of naturally occurring marine metabolite (+)‐frondosin B, an interleukin‐8 inhibitor, has been reassigned. Tf=trifluoromethanesulfonyl.