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Chemistry. 2009;15(12):2747-50. doi: 10.1002/chem.200802568.

Efforts towards the identification of simpler platensimycin analogues--the total synthesis of oxazinidinyl platensimycin.

Author information

1
Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA.

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).

PMID:
19212990
DOI:
10.1002/chem.200802568
[Indexed for MEDLINE]

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