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Stereochemical Definition of the Natural Product (6R,10R,13R, 14R,16R,17R,19S,20S,21R,24S,25S,28S,30S,32R,33R,34R,36S,37S,39R)-Azaspiracid-3 by Total Synthesis and Comparative Analyses.
- Source :
-
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2018 Jan 15; Vol. 57 (3), pp. 810-813. Date of Electronic Publication: 2017 Dec 15. - Publication Year :
- 2018
-
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.<br /> (© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
- Subjects :
- Carbon-13 Magnetic Resonance Spectroscopy
Chromatography, Liquid
Mass Spectrometry
Molecular Structure
Oxidation-Reduction
Proton Magnetic Resonance Spectroscopy
Stereoisomerism
Biological Products chemical synthesis
Biological Products chemistry
Furans chemical synthesis
Furans chemistry
Pyrans chemical synthesis
Pyrans chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1521-3773
- Volume :
- 57
- Issue :
- 3
- Database :
- MEDLINE
- Journal :
- Angewandte Chemie (International ed. in English)
- Publication Type :
- Academic Journal
- Accession number :
- 29193497
- Full Text :
- https://doi.org/10.1002/anie.201711008