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Nature‐Inspired Stereospecific Total Synthesis of P ‐(+)‐Dispegatrine and Four Other Monomeric Sarpagine Indole Alkaloids
Author(s) -
Edwankar Chitra R.,
Edwankar Rahul V.,
Deschamps Jeffrey R.,
Cook James M.
Publication year - 2012
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.201206015
Subject(s) - library science , chemistry , medicine , computer science
All five : The first total synthesis of the C 2 ‐symmetric indole alkaloid 1 involved a late‐stage thallium(III) acetate‐mediated intermolecular oxidative coupling to construct the C9C9′ bond with complete regio‐ and stereocontrol. The formation of a single atropodiastereomer in this critical step arises from internal asymmetric induction. The first total synthesis of four other monomeric sarpagine indole alkaloids is also described.