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

Michael T Taylor; Joseph M Fox

doi:10.1016/j.tetlet.2015.03.009

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

Tetrahedron Lett. 2015 Jun 3;56(23):3560-3563. doi: 10.1016/j.tetlet.2015.03.009.

Authors

Michael T Taylor¹, Joseph M Fox¹

Affiliation

¹ Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, USA.

PMID: 26146420
PMCID: PMC4489422
DOI: 10.1016/j.tetlet.2015.03.009

Abstract

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.

Keywords: biosynthesis; laurepoxide; rearrangement; Δ4-oxocene epoxide.

Grants and funding

S10 OD016267/OD/NIH HHS/United States
R01 GM068650/GM/NIGMS NIH HHS/United States
T32 GM008550/GM/NIGMS NIH HHS/United States
P30 GM110758/GM/NIGMS NIH HHS/United States
S10 RR026962/RR/NCRR NIH HHS/United States
R01 GM068640/GM/NIGMS NIH HHS/United States