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Biosynthesis of the C15-acetogenin laurepoxide may involve bromine-induced skeletal rearrangement of a ?4-oxocene precursor.


ABSTRACT: An electrophilic bromine catalyzed skeletal rearrangement of an ?4-oxocene to an epoxy furan has been described. This skeletal rearrangement suggests a plausible mechanism for the biosynthesis of the C15-acetogenin laurepoxide.

SUBMITTER: Taylor MT 

PROVIDER: S-EPMC4489422 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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Biosynthesis of the C15-acetogenin laurepoxide may involve bromine-induced skeletal rearrangement of a Δ4-oxocene precursor.

Taylor Michael T MT   Fox Joseph M JM  

Tetrahedron letters 20150601 23


An electrophilic bromine catalyzed skeletal rearrangement of an Δ4-oxocene to an epoxy furan has been described. This skeletal rearrangement suggests a plausible mechanism for the biosynthesis of the C15-acetogenin laurepoxide. ...[more]

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