Department of Chemistry and Biochemistry, The Ohio State University, 151 W. Woodruff Ave, Columbus, OH, 43210, USA.
Measurement Science and Standards, National Research Council of Canada, 1411 Oxford St., Halifax, Nova Scotia, B3H 3Z1, Canada.
Angew Chem Int Ed Engl. 2018 Jan 15;57(3):810-813. doi: 10.1002/anie.201711008. Epub 2017 Dec 15.
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.
先前公认的海洋毒素azaspiracid-3 的结构是基于天然产物的原始收敛性和立体选择性全合成进行修订的。本文报道了结构修正假说的提出、验证和证实过程。合成的(6R,10R,13R,14R,16R,17R,19S,20S,21R,24S,25S,28S,30S,32R, 33R,34R,36S,37S,39R)-azaspiracid-3 在色谱和光谱上与天然存在的 azaspiracid-3 相匹配，而之前分配的 20R 对映异构体则不匹配。
