Alkene 1,2-difunctionalization via radical alkenyl migration
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Tang, Xinjun; Studer, Armido (2017). Alkene 1,2-difunctionalization via radical alkenyl migration. Angewandte Chemie International Edition 57 (3), 810-813
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.