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Alkene 1,2-difunctionalization via radical alkenyl migration

dc.contributor.authorTang, Xinjun
dc.contributor.authorStuder, Armido
dc.date.accessioned2018-09-20T16:13:03Z
dc.date.available2018-09-20T16:13:03Z
dc.date.issued2017-11-22
dc.identifier.citationTang, Xinjun; Studer, Armido (2017). Alkene 1,2-difunctionalization via radical alkenyl migration. Angewandte Chemie International Edition 57 (3), 810-813
dc.identifier.issn1433-7851
dc.identifier.urihttp://hdl.handle.net/10379/12238
dc.description.abstractThe previously accepted structure of the marine toxin azaspiracid-3 is revised based upon an original convergent and stereoselective total synthesis of the natural product. The development of a structural revision hypothesis, its testing, and corroboration are reported. Synthetic (6R,10R,13R,14R,16R,17R,19S,20S,21R,24S,25S,28S,30S,32R, 33R,34R,36S,37S,39R)-azaspiracid-3 chromatographically and spectroscopically matched naturally occurring azaspiracid-3, whereas the previously assigned 20R epimer did not.
dc.publisherWiley-Blackwell
dc.relation.ispartofAngewandte Chemie International Edition
dc.rightsAttribution-NonCommercial-NoDerivs 3.0 Ireland
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/3.0/ie/
dc.subjectazaspiracids
dc.subjectnatural products
dc.subjectstructure elucidation
dc.subjecttotal synthesis
dc.subjecttoxins
dc.subjectin-vitro toxicity
dc.subjectlc-ms response
dc.subjectmytilus-edulis
dc.subjectstructural elucidation
dc.subjectconjugate reductions
dc.subjectkinetic resolution
dc.subjectterminal epoxides
dc.subjectcoupling reaction
dc.subjectazaspiracids
dc.subjectshellfish
dc.titleAlkene 1,2-difunctionalization via radical alkenyl migration
dc.typeArticle
dc.identifier.doi10.1002/anie.201710397
dc.local.publishedsourcehttp://europepmc.org/articles/pmc5838557?pdf=render
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Attribution-NonCommercial-NoDerivs 3.0 Ireland
Except where otherwise noted, this item's license is described as Attribution-NonCommercial-NoDerivs 3.0 Ireland