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

Michael T. Taylor
, Joseph M. Fox

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

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.

Original language	English (US)
Article number	46012
Pages (from-to)	3560-3563
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2015.03.009
State	Published - May 25 2015
Externally published	Yes

Keywords

Biosynthesis
Laurepoxide
Rearrangement
Δ4-Oxocene epoxide

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2015.03.009

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

abstract = "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",

author = "Taylor, \{Michael T.\} and Fox, \{Joseph M.\}",

note = "Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd.",

year = "2015",

month = may,

day = "25",

doi = "10.1016/j.tetlet.2015.03.009",

language = "English (US)",

volume = "56",

pages = "3560--3563",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "23",

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TY - JOUR

T1 - Biosynthesis of the C15-acetogenin laurepoxide may involve bromine-induced skeletal rearrangement of a Δ4-oxocene precursor

AU - Taylor, Michael T.

AU - Fox, Joseph M.

PY - 2015/5/25

Y1 - 2015/5/25

N2 - 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.

AB - 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.

KW - Biosynthesis

KW - Laurepoxide

KW - Rearrangement

KW - Δ4-Oxocene epoxide

UR - https://www.scopus.com/pages/publications/84939959599

UR - https://www.scopus.com/pages/publications/84939959599#tab=citedBy

U2 - 10.1016/j.tetlet.2015.03.009

DO - 10.1016/j.tetlet.2015.03.009

M3 - Article

AN - SCOPUS:84939959599

SN - 0040-4039

VL - 56

SP - 3560

EP - 3563

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

M1 - 46012

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

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