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Stereochemical Definition of the Natural Product (6 R ,10 R ,13 R , 14 R ,16 R ,17 R ,19 S ,20 S ,21 R ,24 S ,25 S ,28 S ,30 S ,32 R ,33 R ,34 R ,36 S ,37 S ,39 R )‐Azaspiracid‐3 by Total Synthesis and Comparative Analyses
Author(s) -
Kenton Nathaniel T.,
AduAmpratwum Daniel,
Okumu Antony A.,
McCarron Pearse,
Kilcoyne Jane,
Rise Frode,
Wilkins Alistair L.,
Miles Christopher O.,
Forsyth Craig J.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201711008
Subject(s) - natural product , epimer , stereochemistry , chemistry , stereoselectivity , organic chemistry , catalysis
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 (6 R ,10 R ,13 R ,14 R ,16 R ,17 R ,19 S ,20 S ,21 R ,24 S ,25 S ,28 S ,30 S ,32 R , 33 R ,34 R ,36 S ,37 S ,39 R )‐azaspiracid‐3 chromatographically and spectroscopically matched naturally occurring azaspiracid‐3, whereas the previously assigned 20 R epimer did not.