Spiroacetal formation through telescoped cycloaddition and carbon-hydrogen bond functionalization: total synthesis of
1Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260 (USA).
Abstract:
Spiroacetals can be formed through a one-pot sequence of a hetero-Diels-Alder reaction, an oxidative carbon-hydrogen bond cleavage, and an acid treatment. This convergent approach expedites access to a complex molecular subunit which is present in numerous biologically active structures. The utility of the protocol is demonstrated through its application to a brief synthesis of the actin-binding cytotoxin bistramide A.
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