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Asymmetric total synthesis and structure confirmation of (+)-(3E)-isolaurefucin methyl ether

Abstract:

An asymmetric total synthesis and structure confirmation of (+)-(3E)-isolaurefucin methyl ether (2a) was accomplished. Our synthesis features two complementary routes to construct the α,α’-trans-2,8- dioxabicyclo[5.2.1]decane skeleton of the natural product from α,α’-trans-γ,δ-unsaturated oxocene alcohol 7, namely, an intramolecular epoxide opening route and a novel methoxyetherification route based on organoselenium- mediated oxonium ion formation/fragmentation. A computational analysis was ...

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

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Publisher copy:
10.3987/COM-17-S(T)1

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Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Oxford college:
St Hildas College
Role:
Author
Korean Ministry of Education, Science and Technology More from this funder
John Fell Fund More from this funder
Publisher:
Japan Institute of Heterocyclic Chemistry Publisher's website
Journal:
Heterocycles Journal website
Volume:
97
Issue:
1
Pages:
179-191
Publication date:
2017-11-17
Acceptance date:
2017-11-14
DOI:
EISSN:
1881-0942
ISSN:
0385-5414
Pubs id:
pubs:746822
URN:
uri:58cbaed9-aef9-4157-8160-0415dfcaba19
UUID:
uuid:58cbaed9-aef9-4157-8160-0415dfcaba19
Local pid:
pubs:746822

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