Intermolecular benzyne cycloaddition (IBC) approach to aporphinoids. Total syntheses of norcepharadione B, cepharadione B, dehydroanonaine, duguenaine, …

N Atanes, L Castedo, E Guitián, C Saá…

Index: Atanes, N.; Castedo, L.; Guitian, E.; Saa, C.; Saa, J. M.; Suau, R. Journal of Organic Chemistry, 1991 , vol. 56, # 9 p. 2984 - 2988

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Citation Number: 41

Abstract

MeOH, which produced 5 in high yield, followed by acid treatment (Scheme 111). Compound 5 was later used as an in situ precursor of the somewhat unstable 6 (see Experimental Section for details). Our initial attempts to react la with benzyne (2a) generated from diphenyliodonium carboxylate14 or l-aminobenzotriazo116 were disappointing. It was eventually found that in situ thermal decomposition of an excess benzenediazonium-2- ...