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Asymmetric Total Syntheses of Platensimycin
Author(s) -
Nicolaou K. C.,
Edmonds David J.,
Li Ang,
Tria G. Scott
Publication year - 2007
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.200700586
Subject(s) - cycloisomerization , total synthesis , natural product , alkylation , chemistry , stereochemistry , chiral auxiliary , combinatorial chemistry , enantioselective synthesis , catalysis , organic chemistry
There are two ways about it : One route to the potent antibiotic (−)‐platensimycin used a catalytic asymmetric cycloisomerization and the other an auxiliary‐controlled asymmetric alkylation to set the configuration at a key chiral center (see scheme, TMS=trimethylsilyl). This latter synthesis also used an oxidative dearomatization step to construct a key spirocyclic intermediate en route to the natural product.