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The structure, including stereochemistry, of levorin A1

Abstract

The constitution and stereostructure of levorin A1 1, an aromatic heptaeneantifungal antibiotic, was established on the basis of NMR studies, which contained DQFCOSY,ROESY, HSQC and HMBC experiments. Mycosamine moiety was used as an internalchiral probe to determine the absolute configuration of levorin A1 stereogenic centers: 13S,15R, 17S, 18R, 19S, 21R. The relative configuration of the remaining stereogenic centers wasassigned as follows: 36S*, 37R*, 38S*, 40S* and 41S*. The configuration at C-5 still remainsto be established. The geometry of the heptaene chromophore was defined as 22E, 24E, 26Z,28Z, 30E, 32E and 34E.

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Category:
Articles
Type:
artykuł w czasopiśmie wyróżnionym w JCR
Published in:
MAGNETIC RESONANCE IN CHEMISTRY no. 53, edition 6, pages 479 - 484,
ISSN: 0749-1581
Language:
English
Publication year:
2015
Bibliographic description:
Szwarc K., Szczeblewski P., Sowiński P., Borowski E., Pawlak J.: The structure, including stereochemistry, of levorin A1// MAGNETIC RESONANCE IN CHEMISTRY. -Vol. 53, iss. 6 (2015), s.479-484
DOI:
Digital Object Identifier (open in new tab) 10.1002/mrc.4229
Verified by:
Gdańsk University of Technology

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