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Total Synthesis of Divergolides E and H
Scott M Caplan1, Paul E Floreancig1
1Department of Chemistry, University of Pittsburgh, Pittsburgh, PA, 15260, USA.
Abstract:
This manuscript describes the first total syntheses of divergolides E and H. The route employs a telescoped hetero-Diels-Alder and oxidative carbon-hydrogen bond cleavage as an entry into the central bridged bicyclic acetal unit. Additional key steps of the highly convergent route include a desymmetrizing epoxidation, a chelation-controlled alkenylzinc addition, an amide formation between a hindered aniline and an acylating agent that is prone to ketene formation, and a challenging macrolactonization.
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