Abstract
Herein, we describe a highly efficient formal synthesis of nucleoside antibiotics amipurimycin and 4'-deoxymiharamycin B. A signature event is highlighted by the sequential metal catalysis combining (i) Pd-catalyzed asymmetric hydroalkoxylation of an alkoxyallene; (ii) Ru-catalyzed enyne-methathesis, and (iii) Os-catalyzed dihydroxylation. Remarkably, this atom-efficient sequence allows for the construction of a 3'-branched pyranose core structure in only four steps from readily available Garner's aldehyde.
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