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Alkene 1,2-difunctionalization via radical alkenyl migration

Tang, Xinjun
; 
Studer, Armido
Repository DOI
Publication Date
2017-11-22
Keywords
azaspiracids, natural products, structure elucidation, total synthesis, toxins, in-vitro toxicity, lc-ms response, mytilus-edulis, structural elucidation, conjugate reductions, kinetic resolution, terminal epoxides, coupling reaction, azaspiracids, shellfish
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Article
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Citation
Tang, Xinjun; Studer, Armido (2017). Alkene 1,2-difunctionalization via radical alkenyl migration. Angewandte Chemie International Edition 57 (3), 810-813
Abstract
The 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.
Funder
Publisher
Wiley-Blackwell
Publisher DOI
10.1002/anie.201710397
Rights
Attribution-NonCommercial-NoDerivs 3.0 Ireland
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Externally hosted open access publications with University of Galway authors (2)