Geometry-selective synthesis of the unsaturated side chains of the isodomoic acids

Nadia Fleary-Roberts; Gilles Lemière; Jonathan Clayden

doi:10.1016/j.tet.2015.02.055

Geometry-selective synthesis of the unsaturated side chains of the isodomoic acids

Nadia Fleary-Roberts
, Gilles Lemière
, Jonathan Clayden^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

4 Citations (Scopus)

Abstract

Abstract Three unsaturated vinylic or allylic halides were made in enantiomerically pure form, ready for coupling with a vinyl metal as part of a divergent strategy for the synthesis of members of the domoic/isodomoic acid family and their analogues. The trisubstituted alkene 3 was made by an E-selective Wittig reaction, while 4 and 5 were made by stereoselective hydrometallation or hydroboration of an alkyne.

Original language	English
Pages (from-to)	7204-7208
Number of pages	5
Journal	Tetrahedron
Volume	71
Issue number	39
Early online date	20 Feb 2015
DOIs	https://doi.org/10.1016/j.tet.2015.02.055
Publication status	Published - 30 Sept 2015

Research Groups and Themes

Organic & Biological

Keywords

Alkene
Coupling
Metalcatalysed
Natural product synthesis

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10.1016/j.tet.2015.02.055

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title = "Geometry-selective synthesis of the unsaturated side chains of the isodomoic acids",

abstract = "Abstract Three unsaturated vinylic or allylic halides were made in enantiomerically pure form, ready for coupling with a vinyl metal as part of a divergent strategy for the synthesis of members of the domoic/isodomoic acid family and their analogues. The trisubstituted alkene 3 was made by an E-selective Wittig reaction, while 4 and 5 were made by stereoselective hydrometallation or hydroboration of an alkyne.",

keywords = "Alkene, Coupling, Metalcatalysed, Natural product synthesis",

author = "Nadia Fleary-Roberts and Gilles Lemi{\`e}re and Jonathan Clayden",

year = "2015",

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day = "30",

doi = "10.1016/j.tet.2015.02.055",

language = "English",

volume = "71",

pages = "7204--7208",

journal = "Tetrahedron",

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TY - JOUR

T1 - Geometry-selective synthesis of the unsaturated side chains of the isodomoic acids

AU - Fleary-Roberts, Nadia

AU - Lemière, Gilles

AU - Clayden, Jonathan

PY - 2015/9/30

Y1 - 2015/9/30

N2 - Abstract Three unsaturated vinylic or allylic halides were made in enantiomerically pure form, ready for coupling with a vinyl metal as part of a divergent strategy for the synthesis of members of the domoic/isodomoic acid family and their analogues. The trisubstituted alkene 3 was made by an E-selective Wittig reaction, while 4 and 5 were made by stereoselective hydrometallation or hydroboration of an alkyne.

AB - Abstract Three unsaturated vinylic or allylic halides were made in enantiomerically pure form, ready for coupling with a vinyl metal as part of a divergent strategy for the synthesis of members of the domoic/isodomoic acid family and their analogues. The trisubstituted alkene 3 was made by an E-selective Wittig reaction, while 4 and 5 were made by stereoselective hydrometallation or hydroboration of an alkyne.

KW - Alkene

KW - Coupling

KW - Metalcatalysed

KW - Natural product synthesis

UR - https://www.scopus.com/pages/publications/84939255057

U2 - 10.1016/j.tet.2015.02.055

DO - 10.1016/j.tet.2015.02.055

M3 - Article (Academic Journal)

AN - SCOPUS:84939255057

SN - 0040-4020

VL - 71

SP - 7204

EP - 7208

JO - Tetrahedron

JF - Tetrahedron

IS - 39

ER -

Geometry-selective synthesis of the unsaturated side chains of the isodomoic acids

Abstract

Research Groups and Themes

Keywords

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