Stereochemistry of spongosoritins: beyond optical rotation.
Org Biomol Chem
; 17(45): 9772-9777, 2019 12 07.
Article
em En
| MEDLINE
| ID: mdl-31710062
ABSTRACT
Stereochemical determinations based solely on the comparison of optical rotation (OR) measured at a single wavelength may commonly result in misassignments. Herein, we use vibrational and electronic CD, NMR, OR, and DFT calculations, to confirm the absolute configuration (AC) of the cytotoxic marine polyketides spongosoritin A (1) and 9,10-dihydrospongosoritin A (2) as (-)-(6R,8R) and (-)-(6R,8S), respectively. The AC of natural 1 and 2 has so far relied upon comparisons of OR values only. Besides showing the dependence of OR on achiral structural features, such as E/Z double bond geometries, an IR spectral marker is provided to help distinguish the geometric isomers of related molecules.
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Coleções:
01-internacional
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MEDLINE
Idioma:
En
Ano de publicação:
2019
Tipo de documento:
Article