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- W2950358191 abstract "Herein we report the first total synthesis of Penifulvin A, a sesquiterpenoid with a novel dioxa-fenestrane structure. Penifulvin A is a potent insecticide against the fall armyworm Spodoptera frugiperda which causes enormous damage in the US by consuming foliage of a variety of field crops. A five-step racemic and an eight-step enantioselective route to the natural product and the determination of its absolute configuration are described. The key step involves a meta-photocycloaddition, giving rapid access to the carbon skeleton of penifulvin A in a stereoselective fashion. Finally an oxidation cascade leads to the natural product. The synthetic route is free from protecting groups, scalable, and flexible so that a variety of analogues, among them penifulvins B−E, should be available for performing SAR tests in the insecticidal role." @default.
- W2950358191 created "2019-06-27" @default.
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- W2950358191 date "2008-12-19" @default.
- W2950358191 modified "2023-10-17" @default.
- W2950358191 title "Total Synthesis of (−)-Penifulvin A, an Insecticide with a Dioxafenestrane Skeleton" @default.
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- W2950358191 doi "https://doi.org/10.1021/ja8083048" @default.
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