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Synthesis of the Louisianin Alkaloid Family via a 1,2,4-Triazine Inverse-Electron-Demand Diels-Alder Approach

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Publication details

JournalJournal of Organic Chemistry
DatePublished - 6 Nov 2009
Issue number21
Volume74
Number of pages12
Pages (from-to)8343-8354
Original languageEnglish

Abstract

Isolated in 1995, the four members of the louisianin family (A, B, C and D) are simple pyridine and 2-pyridone alkaloids that display both antibacterial and anticancer activity. Herein we describe the synthesis of all four members of the louisianin family, from I conveniently prepared 1,2,4-triazine and via I common tetrasubstituted pyridine intermediate. This study includes the synthesis of louisianin B in both racemic form and is the (-)-enantiomer.

    Research areas

  • HIGHLY SUBSTITUTED PYRIDINES, ASYMMETRIC TRANSFER HYDROGENATION, NONSTEROIDAL GROWTH-INHIBITORS, BAEYER-VILLIGER OXIDATION, RESPONSIVE SC-115 CELLS, HETEROCYCLIC AZADIENES, THIOHYDROXAMIC ESTERS, EFFICIENT SYNTHESIS, TANDEM OXIDATION, CARBOXYLIC-ACIDS

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