Total synthesis based on the originally claimed structure of mucosin

The first total synthesis aimed at the naturally occurring eicosanoid bicycle mucosin is reported. A practical route has been devised allowing the issues relating to the previous assignment of stereochemistry to be examined. X-ray crystallography was performed on a late stage intermediate to pinpoin...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 14; no. 36; pp. 8433 - 8437
Main Authors Gallantree-Smith, Harrison C., Antonsen, Simen G., Gorbitz, Carl H., Hansen, Trond V., Nolsoe, Jens M. J., Stenstrom, Yngve H.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SYNTHASE
OXYLIPINS
HYDROBORATION
ALGA GRACILARIOPSIS-LEMANEIFORMIS
HYDROZIRCONATION
NATURAL-PRODUCTS
BIOSYNTHESIS
DIELS-ALDER REACTION
FATTY-ACIDS
CONJUGATE ADDITION
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Summary:The first total synthesis aimed at the naturally occurring eicosanoid bicycle mucosin is reported. A practical route has been devised allowing the issues relating to the previous assignment of stereochemistry to be examined. X-ray crystallography was performed on a late stage intermediate to pinpoint the topological relationship displayed by the featured bicyclo[4.3.0]non-3-ene scaffold.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob01511e