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Efforts towards the Identification of Simpler Platensimycin Analogues—The Total Synthesis of Oxazinidinyl Platensimycin

✍ Scribed by Jingxin Wang; Vincent Lee; Herman O. Sintim

Publisher: John Wiley and Sons
Year: 2009
Tongue: English
Weight: 212 KB
Volume: 15
Category: Article
ISSN: 0947-6539
DOI: 10.1002/chem.200802568

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✦ Synopsis

Abstract

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).magnified image

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