The asymmetric total syntheses of daumone , daumone along with 5 new analogs are described. The key steps of our approach are: the diastereoselective palladium catalyzed glycosylation reaction; the Noyori reduction of 2-acetylfuran and an ynone, which introduce the absolute stereochemistry of the sugar and aglycon portion of daumone; and an Achmatowicz rearrangement, an epoxidation and a ring opening installing the remaining asymmetry of daumone. The synthetic daumones and as well as related analogs were evaluated for dauer activity in and for effects on hatching of the related nematode . This data provides additional structure activity relationships (SAR) that further inform the study of nematode signaling.
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| http://dx.doi.org/10.1016/j.tet.2016.03.033 | DOI Listing |
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