Total synthesis of the β-adrenergic receptor antagonist, the tetrahydroisoquinoline MY336-a and its epimer

TS Kaufman

Index: Kaufman, Teodoro S. Journal of the Chemical Society - Perkin Transactions 1, 1996 , # 20 p. 2497 - 2505

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Citation Number: 27

Abstract

The first total synthesis of the novel β-adrenergic receptor antagonist MY336-a 1 and its epimer 2 has been achieved from 2, 3-dimethoxytoluene, by Jackson cyclisation of Nbenzyl- N-tosylamido acetals, Lewis acid-mediated addition of silicon-based nucleophiles to p- tosyliminium ions and base-catalysed epimerisation of 1-substituted hydroxytetrahydroisoquinolines, being key steps.