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 | Zendy

Kenton Nathaniel T. | Zendy; AduAmpratwum Daniel | Zendy; Okumu Antony A. | Zendy; McCarron Pearse | Zendy; Kilcoyne Jane | Zendy; Rise Frode | Zendy; Wilkins Alistair L. | Zendy; Miles Christopher O. | Zendy; Forsyth Craig J. | Zendy

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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.

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