Total synthesis of phomazarin

DL Boger, J Hong, M Hikota…

Index: Boger, Dale L.; Hong, Jiyong; Hikota, Masataka; Ishida, Michio Journal of the American Chemical Society, 1999 , vol. 121, # 11 p. 2471 - 2477

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Citation Number: 85

Abstract

A concise total synthesis of phomazarin (1) is detailed enlisting a heterocyclic azadiene inverse electron demand Diels-Alder reaction (1, 2, 4-triazine→ pyridine) for preparation of the fully substituted and appropriately functionalized pyridine C-ring. Thus,[4+ 2] cycloaddition (85%) of triethyl 1, 2, 4-triazine-3, 5, 6-tricarboxylate (2) with trimethoxyethylene (3) followed by conversion of the cycloadduct 11 to the cyclic ...