Eintrag weiter verarbeiten
Syntheses of a Pair of Simplified Model Compounds of the Dihydroxycyclopentenone Core of the Kodaistatins A–D
Gespeichert in:
Personen und Körperschaften: | , |
---|---|
Titel: |
Syntheses of a Pair of Simplified Model Compounds of the Dihydroxycyclopentenone Core of the Kodaistatins A–D |
In: | European Journal of Organic Chemistry, 2018, 2018, 45, S. 6256-6273 |
veröffentlicht: |
Wiley
|
Umfang: | 6256-6273 |
ISSN: |
1099-0690 1434-193X |
DOI: | 10.1002/ejoc.201801117 |
Zusammenfassung: | <jats:p>The kodaistatins A–D (<jats:bold>1–4</jats:bold>) are natural products from <jats:italic>Aspergillus terreus</jats:italic> with the potential of representing leads for a novel cure of type‐2 diabetes. They possess an unusually and highly substituted dihydroxycyclopentenone core. Whether its OH groups are <jats:italic>cis</jats:italic>‐ or <jats:italic>trans</jats:italic>‐configured remained unknown by spectroscopy. Previous syntheses of kodaistatin model compounds (<jats:italic>cis</jats:italic>‐<jats:bold>5</jats:bold>, <jats:italic>cis</jats:italic>‐ and <jats:italic>trans</jats:italic>‐<jats:bold>6</jats:bold>) allowed to make NMR comparisons with kodaistatin A (<jats:bold>1</jats:bold>). They led to the insight that the natural product <jats:bold>1</jats:bold> must be a <jats:italic>trans</jats:italic>‐diol. These findings are corroborated by the synthesis and ensuing NMR study of another pair of <jats:italic>cis/trans</jats:italic>‐isomeric kodaistatin models (<jats:italic>cis</jats:italic>‐ and <jats:italic>trans</jats:italic>‐<jats:bold>7</jats:bold>) described here. Its first key‐step was a <jats:italic>syn</jats:italic>‐selective aldol addition. An oxidation/reduction sequence allowed reaching to the corresponding <jats:italic>anti</jats:italic>‐aldol. Each aldol furnished a kodaistatin model in eight additional steps. The most noteworthy transformation was an Sm<jats:sup>II</jats:sup>‐induced intramolecular aldolization of a bromodiketone.</jats:p> |
Format: | E-Article |
Quelle: | Wiley (CrossRef) |
Sprache: | Englisch |