Total synthesis of (6R,10R,13R,14R,16R,17R,19S,20R,21R,24S, 25S,28S,30S,32R,33R,34R,36S,37S,39R)-azaspiracid-3 reveals non-identity with the natural product

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  1. Get@NRC: Total synthesis of (6R,10R,13R,14R,16R,17R,19S,20R,21R,24S, 25S,28S,30S,32R,33R,34R,36S,37S,39R)-azaspiracid-3 reveals non-identity with the natural product (Opens in a new window)
DOIResolve DOI: http://doi.org/10.1002/ange.201711006
AuthorSearch for: ; Search for: ; Search for: ; Search for: ; Search for: ; Search for: ; Search for: ; Search for: ; Search for: ; Search for: ; Search for: ; Search for: ; Search for: ; Search for:
TypeArticle
Journal titleAngewandte Chemie
ISSN0044-8249
Subjectazaspiracids; total synthesis; structure determination; natural products; toxins
AbstractA convergent and stereoselective total synthesis of the previously assigned structure of azaspiracid-3 has been achieved via a late stage NHK coupling to form the C21‒C22 bond with the C20 configuration unambiguously established from L-(+)-tartaric acid. Post-coupling steps involved oxidation to an ynone, modified Stryker reduction of the alkyne, global deprotection, and oxidation of the primary alcohol to the carboxylic acid. The synthetic product matched naturally occurring azaspiracid-3 by mass spectrometry, but differed both chromatographically and spectroscopically.
Publication date
PublisherWiley
LanguageEnglish
AffiliationMeasurement Science and Standards; National Research Council Canada
Peer reviewedYes
NPARC number23002591
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Record identifier293d5dfa-8dd0-4fa8-b7f5-6ce4c2d17a02
Record created2017-12-04
Record modified2017-12-04
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