Concise total syntheses of the anthracenone C-glycosides Alvaradoins E and F, Uveoside, and 10-epi-Uveoside (1-4), have been accomplished in 11 steps each from chrysophanic acid 5 and protected bromosugar 6. Key steps in the synthetic pathways include the DBU-induced coupling of 5 and 6 to stereoselectively produce a β-C-glycoside, and the Pb(OAc)4-mediated Kochi reaction to introduce the C.1’ oxygen atom of the natural products.

Total synthesis of alvaradoins E and F, uveoside, and 10-epi-uveoside

2019 Fall National Meeting

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