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

TY - JOUR

T1 - Synthesis of the Louisianin Alkaloid Family via a 1,2,4-Triazine Inverse-Electron-Demand Diels-Alder Approach

AU - Catozzi, Nicola

AU - Edwards, Michael G.

AU - Raw, Steven A.

AU - Wasnaire, Pierre

AU - Taylor, Richard J. K.

PY - 2009/11/6

Y1 - 2009/11/6

N2 - 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.

AB - 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.

KW - HIGHLY SUBSTITUTED PYRIDINES

KW - ASYMMETRIC TRANSFER HYDROGENATION

KW - NONSTEROIDAL GROWTH-INHIBITORS

KW - BAEYER-VILLIGER OXIDATION

KW - RESPONSIVE SC-115 CELLS

KW - HETEROCYCLIC AZADIENES

KW - THIOHYDROXAMIC ESTERS

KW - EFFICIENT SYNTHESIS

KW - TANDEM OXIDATION

KW - CARBOXYLIC-ACIDS

UR - http://www.scopus.com/inward/record.url?scp=70350707662&partnerID=8YFLogxK

U2 - 10.1021/jo901761r

DO - 10.1021/jo901761r

M3 - Article

SN - 0022-3263

VL - 74

SP - 8343

EP - 8354

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 21

ER -