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Total Synthesis and Absolute Configuration of Macrocidin A, a Cyclophane Tetramic Acid Natural Product
Author(s) -
Yoshinari Tomohiro,
Ohmori Ken,
Schrems Marcus G.,
Pfaltz Andreas,
Suzuki Keisuke
Publication year - 2010
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.200906362
Subject(s) - cyclophane , ketene , chemistry , intramolecular force , iridium , ring (chemistry) , stereochemistry , catalysis , medicinal chemistry , molecule , organic chemistry
Stereocontrolled access to the cyclophane framework of macrocidin A has been achieved for the first time. The key steps include the iridium‐catalyzed asymmetric hydrogenation without fission of the CI bond, the macrolactam formation by intramolecular ketene trapping, and the Lacey–Dieckmann cyclization for the construction of the tetramic acid ring.