Total Synthesis of (−)-Penifulvin A, an Insecticide with a Dioxafenestrane Skeleton

Gaich, Tanja; Mulzer, Johann

Total Synthesis of (−)-Penifulvin A, an Insecticide with a Dioxafenestrane Skeleton

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Datum

2009

Autor:innen

Gaich, Tanja

Mulzer, Johann

DOI (zitierfähiger Link)

https://doi.org/10.1021/ja8083048

Sammlungen

Chemie

Publikationstyp

Zeitschriftenartikel

Publikationsstatus

Published

Erschienen in

Journal of the American Chemical Society. 2009, 131(2), pp. 452-453. ISSN 0002-7863. eISSN 1520-5126. Available under: doi: 10.1021/ja8083048

Zusammenfassung

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.

Fachgebiet (DDC)

540 Chemie

Zitieren

ISO 690

GAICH, Tanja, Johann MULZER, 2009. Total Synthesis of (−)-Penifulvin A, an Insecticide with a Dioxafenestrane Skeleton. In: Journal of the American Chemical Society. 2009, 131(2), pp. 452-453. ISSN 0002-7863. eISSN 1520-5126. Available under: doi: 10.1021/ja8083048

BibTex

@article{Gaich2009Total-40711,
  year={2009},
  doi={10.1021/ja8083048},
  title={Total Synthesis of (−)-Penifulvin A, an Insecticide with a Dioxafenestrane Skeleton},
  number={2},
  volume={131},
  issn={0002-7863},
  journal={Journal of the American Chemical Society},
  pages={452--453},
  author={Gaich, Tanja and Mulzer, Johann}
}

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Universitätsbibliographie

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