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Efforts towards the Identification of Simpler Platensimycin Analogues—The Total Synthesis of Oxazinidinyl Platensimycin
Author(s) -
Wang Jingxin,
Lee Vincent,
Sintim Herman O.
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200802568
Subject(s) - epimer , chemistry , epoxide , metathesis , intramolecular force , ring closing metathesis , stereochemistry , combinatorial chemistry , ring (chemistry) , catalysis , organic chemistry , polymer , polymerization
Epimerization and stapling in one pot : A facile synthesis of an oxazinidinyl analogue of the antibiotic platensimycin is presented. Key steps of this work are a novel dynamic ring‐closing metathesis (RCM) that involves a base‐catalyzed epimerization followed by a tandem Ru‐catalyzed metathesis, and a nucleophilic addition to a ketone followed by a subsequent intramolecular epoxide ring‐opening reaction to construct the core structure of the target molecule (see scheme).