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Published on: August 1, 2018
Flexible Total Synthesis of (±)-Aureothin, a Potent Antiproliferative Agent
Matthias Henrot1, Alexandre Jean1, Philippe A Peixoto1
1COBRA-IRCOF, CNRS, Université & INSA de Rouen , Mont Saint Aignan, France.
Abstract:
Amenable to late-stage preparation of analogues, a flexible and convergent total synthesis of (±)-aureothin is presented. The strategy was based on a desymmetrization of α,α'-dimethoxy-γ-pyrone by a process combining 1,4-addition and alkylation of vinylogous enolate to stereoselectively reach the backbone of the target. Palladium-catalyzed cyanation of an elaborated and isomerizable E,Z dienyl motif followed by Pinner cyclization enabled the construction of the tetrahydrofuran motif while a first approach based on a late-stage oxidation was unsuccessful.
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