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Alkene protection against acid using a bromide substituent: application in a total synthesis of (−)-6,7-dideoxysqualestatin H5

Abstract:

The presence of a bromide substituent, instead of a hydrogen or methyl group, on a carbon–carbon double bond, protects the alkene from addition reactions when exposed to trifluoroacetic acid. This concept is used to circumvent concomitant loss of unsaturation in a late-stage acid-catalysed 6,8- to 2,8-dioxabicyclo[3.2.1]octane rearrangement towards (−)-6,7-dideoxysqualestatin H5. The inertness of the alkenyl bromide functionality is demonstrated through several synthetic transformations in th...

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Publication status:
Published
Peer review status:
Peer reviewed
Version:
Accepted Manuscript

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Publisher copy:
10.1039/C8CC02690D

Authors


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Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Al Mamari, HH More by this author
Sintim, HO More by this author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Oxford college:
Oriel College
Higher Committee for Education Development in Iraq More from this funder
Sultanate of Oman More from this funder
University of Oxford More from this funder
More from this funder
Grant:
Marie Curie Fellowship (MEIF-CT-2004-515366 to A. V.)
Publisher:
Royal Society of Chemistry Publisher's website
Journal:
Chemical Communications Journal website
Volume:
54
Issue:
42
Pages:
5354-5356
Publication date:
2018-05-09
Acceptance date:
2018-05-03
DOI:
EISSN:
1364-548X
ISSN:
1359-7345
Pubs id:
pubs:845765
URN:
uri:299def8a-02e7-43fa-99cd-431a8575dfc6
UUID:
uuid:299def8a-02e7-43fa-99cd-431a8575dfc6
Local pid:
pubs:845765

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