Tetrahedron Letters

Practical synthesis of a functionalized 1-oxo-1, 2, 3, 4-tetrahydroisoquinoline-3-carboxylic acid

SAP Quintiliano, LF Silva

Index: Quintiliano, Samir A.P.; Silva Jr., Luiz F. Tetrahedron Letters, 2012 , vol. 53, # 29 p. 3808 - 3810

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Citation Number: 3

Abstract

The synthesis of a functionalized 1-oxo-1, 2, 3, 4-tetrahydroisoquinoline-3-carboxylic acid has been performed in 10 steps from the readily available dimedone. Only three purifications by flash chromatography are required through the whole sequence. The key step is the reaction between a dimedone derivative and a chlorotetrolic ester, that gives a tetrasubstituted benzene ring (through a Diels–Alder/retro-Diels–Alder process) bearing ...