18O Assisted Analysis of a γ,δ-epoxyketone Cyclization: Synthesis of the C16-C28 Fragment of Ammocidin D
Overview
Overview
Journal
Org Lett
Publisher
American Chemical Society
Specialties
Biochemistry
Chemistry
Chemistry
Date
2011 Jan 21
PMID
21247077
Authors
Affiliations
Affiliations
Soon will be listed here.
Abstract
The C16-C28 fragment common to the cytotoxic macrolide ammocidin D has been prepared by a stereospecific 5-exo closure of a γ,δ-epoxyketone followed by a rearrangement to a pyran acetal. The reaction pathway was traced by (18)O labeling of the keto carbonyl and observation of (18)O induced (13)C shifts in the pyran acetal product. NMR data of the synthetic C16-C28 fragment compared favorably to the natural product providing support of the assigned stereochemistry.
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