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- W2890782137 abstract "The kodaistatins A–D ( 1–4 ) are natural products from Aspergillus terreus 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 cis ‐ or trans ‐configured remained unknown by spectroscopy. Previous syntheses of kodaistatin model compounds ( cis ‐ 5 , cis ‐ and trans ‐ 6 ) allowed to make NMR comparisons with kodaistatin A ( 1 ). They led to the insight that the natural product 1 must be a trans ‐diol. These findings are corroborated by the synthesis and ensuing NMR study of another pair of cis/trans ‐isomeric kodaistatin models ( cis ‐ and trans ‐ 7 ) described here. Its first key‐step was a syn ‐selective aldol addition. An oxidation/reduction sequence allowed reaching to the corresponding anti ‐aldol. Each aldol furnished a kodaistatin model in eight additional steps. The most noteworthy transformation was an Sm II ‐induced intramolecular aldolization of a bromodiketone." @default.
- W2890782137 created "2018-09-27" @default.
- W2890782137 creator A5026257543 @default.
- W2890782137 creator A5032839055 @default.
- W2890782137 date "2018-11-27" @default.
- W2890782137 modified "2023-09-25" @default.
- W2890782137 title "Syntheses of a Pair of Simplified Model Compounds of the Dihydroxycyclopentenone Core of the Kodaistatins A-D" @default.
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- W2890782137 doi "https://doi.org/10.1002/ejoc.201801117" @default.
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