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Feldman KS, Quideau S, Appel HM. Galloyl-Derived Orthoquinones as Reactive Partners in Nucleophilic Additions and Diels-Alder Dimerizations: A Novel Route to the Dehydrodigalloyl Linker Unit of Agrimoniin-Type Ellagitannins. J Org Chem. 1996;61(19):6656-6665doi: 10.1021/jo961043u.
Feldman, K. S., Quideau, S., & Appel, H. M. (1996). Galloyl-Derived Orthoquinones as Reactive Partners in Nucleophilic Additions and Diels-Alder Dimerizations: A Novel Route to the Dehydrodigalloyl Linker Unit of Agrimoniin-Type Ellagitannins. The Journal of organic chemistry, 61(19), 6656-6665. https://doi.org/10.1021/jo961043u
Feldman, Ken S., et al. "Galloyl-Derived Orthoquinones as Reactive Partners in Nucleophilic Additions and Diels-Alder Dimerizations: A Novel Route to the Dehydrodigalloyl Linker Unit of Agrimoniin-Type Ellagitannins." The Journal of organic chemistry vol. 61,19 (1996): 6656-6665. doi: https://doi.org/10.1021/jo961043u
Feldman KS, Quideau S, Appel HM. Galloyl-Derived Orthoquinones as Reactive Partners in Nucleophilic Additions and Diels-Alder Dimerizations: A Novel Route to the Dehydrodigalloyl Linker Unit of Agrimoniin-Type Ellagitannins. J Org Chem. 1996 Sep 20;61(19):6656-6665. doi: 10.1021/jo961043u. PMID: 11667537.
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J Org Chem. 1996 Sep 20;61(19):6656-6665. doi: 10.1021/jo961043u.

Galloyl-Derived Orthoquinones as Reactive Partners in Nucleophilic Additions and Diels-Alder Dimerizations: A Novel Route to the Dehydrodigalloyl Linker Unit of Agrimoniin-Type Ellagitannins.

The Journal of organic chemistry

Ken S. Feldman, Stéphane Quideau, Heidi M. Appel

Affiliations

  1. Department of Chemistry and Pesticide Research Laboratory, The Pennsylvania State University, University Park, Pennsylvania 16802.

PMID: 11667537 DOI: 10.1021/jo961043u

Abstract

Orthochloranil-mediated oxidation of galloyl monoethers furnishes the derived orthoquinones in excellent yield. These reactive electrophiles participate in a variety of nucleophilic addition reactions with heteroatomic and carbanionic partners. In addition, Lewis acid-mediated dimerization of the orthoquinones provides an efficient route to dehydrodigalloyl-type diaryl ether units characteristic of several ellagitannin natural products. The implications for ellagitannin biosynthesis and gallotannin-protein covalent attachment are discussed.

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