Stereocontrolled regeneration of olefins from epoxides

Veronica S Wills; Xiang Zhou; Cheryl Allen; Sarah A Holstein; David F Wiemer

doi:10.1016/j.tetlet.2016.02.041

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Stereocontrolled regeneration of olefins from epoxides

Journal article

Peer reviewed

Stereocontrolled regeneration of olefins from epoxides

Veronica S Wills, Xiang Zhou, Cheryl Allen, Sarah A Holstein and David F Wiemer

Tetrahedron letters, Vol.57(12), pp.1335-1337

03/23/2016

DOI: 10.1016/j.tetlet.2016.02.041

PMCID: PMC4778745

PMID: 26955189

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Abstract

[Display omitted] Through treatment with NaI and trifluoroacetic anhydride, which presumably forms trifluoroacetyl iodide in situ, epoxides can be converted to olefins. This reaction now has been shown to tolerate remote olefins without loss of their individual stereochemistry. A reaction sequence involving regiospecific epoxidation of an isoprenoid alcohol, conversion of the alcohol to an azide, and cycloaddition with an acetylene, followed by conversion of the epoxide back to the original olefin, has allowed stereocontrolled preparation of triazole bisphosphonates with a farnesyl or a geranylgeranyl substituent. This strategy may be applicable for selective protection of an alkene in other polyolefins, including substrates for metathesis reactions.

Triazole

Phosphonate

Epoxide

Deoxygenation

Details

Title: Subtitle: Stereocontrolled regeneration of olefins from epoxides
Creators: Veronica S Wills - Department of Chemistry, The University of Iowa, 52242-1294, USA
Xiang Zhou - Department of Chemistry, The University of Iowa, 52242-1294, USA
Cheryl Allen - Roswell Park Cancer Institute
Sarah A Holstein - Department of Medicine, Roswell Park Cancer Institute, Buffalo, NY 14263, USA
David F Wiemer - Department of Chemistry, The University of Iowa, 52242-1294, USA
Resource Type: Journal article
Publication Details: Tetrahedron letters, Vol.57(12), pp.1335-1337
DOI: 10.1016/j.tetlet.2016.02.041
PMID: 26955189
PMCID: PMC4778745
NLM abbreviation: Tetrahedron Lett
ISSN: 0040-4039
eISSN: 1873-3581
Publisher: Elsevier Ltd
Grant note: name: UI Graduate College, award: T32 GM008365; DOI: 10.13039/100000002, name: NIH, award: R01CA-172070; DOI: 10.13039/100001422, name: American Society of Hematology; DOI: 10.13039/100001024, name: Roy J. Carver Charitable Trust
Language: English
Date published: 03/23/2016
Academic Unit: Neuroscience and Pharmacology; Chemistry
Record Identifier: 9983985988202771

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