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Issue 0, 1966
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Stereochemistry and biogenesis of mopanols and peltogynols and associated flavanoids from Colophospermum mopane

Abstract

(+)-Mopanol and its 4-epimer (mopanol B) from mopane heartwood are shown to have the same relative and absolute configurations as the accompanying isomeric and identically related pair, (+)-peltogynol and peltogynol B. The relative configurations of the peltogynols (2,3-trans-3,4-trans and 2,3-trans-3,4-cis, respectively) are confirmed by nuclear magnetic resonance spectroscopy of their derivatives. The absolute configurations of (+)-mopanol and (+)-peltogynol are revised to 2R,3S,4R, following comparison of (+)-mopanone with (+)-fustin by optical rotatory dispersion methods. Accordingly, (+)-mopanol B and (+)-peltogynol B have the 2R,3S,4S configuration. The difference between isomeric mopanols and peltogynols is confined to a variation in the C-linked substitution of their catechol nuclei.

This structural relationship, their concomitance, and the association with (–)-fisetinidol and the new compound (+)-epifisetinidol and (+)-3′,4′7,-trihydroxy-2,3-trans-flavan-3,4-cis-diol, indicates the common biogenetic origins of mopanols and peltogynols in the reaction of formaldehyde with mutual 2,3-trans-3,4-trans and 2,3-trans-3,4-cis leucofisetinidin precursors.

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Article information


J. Chem. Soc. C, 1966, 1644-1653
Article type
Paper

Stereochemistry and biogenesis of mopanols and peltogynols and associated flavanoids from Colophospermum mopane

S. E. Drewes and D. G. Roux, J. Chem. Soc. C, 1966, 1644
DOI: 10.1039/J39660001644

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