Journal of the American Chemical Society

Total synthesis of nothapodytine B and (-)-mappicine

DL Boger, J Hong

Index: Boger, Dale L.; Hong, Jiyong Journal of the American Chemical Society, 1998 , vol. 120, # 6 p. 1218 - 1222

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Citation Number: 62

Abstract

Concise total syntheses of naturally occurring nothapodytine B (1, mappicine ketone) and (-)- mappicine (3) are detailed. The approach is based on the implementation of a room- temperature, inverse electron demand Diels-Alder reaction of the N-sulfonyl-1-aza-1, 3- butadiene 11 for assemblage of a pyridone D ring precursor central to the structure. A Friedlander condensation is utilized for constructing the AB ring system of 1 and 3. An acid ...