Absolute configurations of isoflavans |
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| Authors: | Kazu Kurosawa WDavid Ollis Brian T Redman Ian O Sutherland Herbert M Alves Otto R Gottlieb |
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| Institution: | 1. Department of Chemistry, The University, Sheffield S3 7HF, England;2. Instituto de Ciêndias Exatas, Universidade Federal de Minas Gerais, Belo Horizonte, Brasil;3. Instituto de Química, Universidade de São Paulo, c.p. 20780, São Paulo, Brasil |
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| Abstract: | The absolute configurations of isoflavans and isoflavanquinones isolated from Cyclolobium, Dalbergia and Machaerium species were established by comparison of their ORD curves with that of (3S)-5,7,3′,4′-tetra-methoxyisoflavan and (3S)-7,4′-dimethoxyisoflavan-2′,5′-quinone, respectively. The assignments were checked by the ozonolysis of the isoflavan (?)-duartin to (R)-paraconic acid and the oxidation of isoflavans to isoflavanquinones. The PMR spectra of the dihydropyran ring of the isoflavans are discussed in terms of the preferred conformation of this ring. |
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| Keywords: | Leguminosae-Lotoideae isoflavans isoflavanquinones absolute configurations |
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