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Stereochemistry of spongosoritins: beyond optical rotation

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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.

Graphical abstract: Stereochemistry of spongosoritins: beyond optical rotation

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Publication details

The article was received on 16 Sep 2019, accepted on 29 Oct 2019 and first published on 29 Oct 2019


Article type: Paper
DOI: 10.1039/C9OB02010A
Org. Biomol. Chem., 2019, Advance Article

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    Stereochemistry of spongosoritins: beyond optical rotation

    A. N. L. Batista, F. M. dos Santos, A. L. Valverde and J. M. Batista, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB02010A

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