Synthesis of a potent (±)-4-(2-hydroxyphenyl) analogue of the acromelic acids by dearomatising cyclisation of a lithiated Np-methoxybenzyl-4-methoxy-1-naphthamide

A Ahmed, RA Bragg, J Clayden, K Tchabanenko

Index: Ahmed, Anjum; Bragg, Ryan A; Clayden, Jonathan; Tchabanenko, Kirill Tetrahedron Letters, 2001 , vol. 42, # 20 p. 3407 - 3410

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Citation Number: 57

Abstract

Dearomatising anionic cyclisation of N-cumyl-Np-methoxybenzyl-4-methoxy-1-naphthamide 8 diastereoselectively generates a pyrrolidinone-fused tetralone 12 which may be transformed in seven steps to the racemic form of a known non-natural member of the aryl kainoid family 4 having potent biological activity. Key steps of the synthesis are ruthenium- catalysed oxidation of the C2-p-methoxybenzyl ring of 12 to a carboxylic acid and Baeyer– ...