Ontology highlight
ABSTRACT:
SUBMITTER: Chau ST
PROVIDER: S-EPMC3079550 | biostudies-literature | 2011 Feb
REPOSITORIES: biostudies-literature
Chau Stephen T ST Hayakawa Yoichi Y Sulikowski Gary A GA
Organic letters 20110119 4
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. ...[more]