期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 17, 期 45, 页码 9772-9777出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9ob02010a
关键词
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资金
- Sao Paulo Research Foundation - FAPESP [2014/25222-9]
- National Counsel of Technological and Scientific Development - CNPq [431978/2018-2]
- Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior - Brasil (CAPES) [001]
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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