Enantioselective total syntheses of (+)-arborescidine A,(-)-arborescidine B, and (-)-arborescidine C

LS Santos, RA Pilli, VH Rawal

Index: Santos, Leonardo S.; Pilli, Ronaldo A.; Rawal, Viresh H. Journal of Organic Chemistry, 2004 , vol. 69, # 4 p. 1283 - 1289

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Citation Number: 71

Abstract

Described are the first enantioselective total syntheses of (+)-arborescidine A ((+)-1),(-)- arborescidine B ((-)-2), and (-)-arborescidine C ((-)-3), via routes that proceeded in five steps and 50% overall yield, eight steps and 61% overall yield, and nine steps and 51% overall yield, respectively, from 6-bromotryptamine (7). The syntheses feature the use of the Noyori catalytic asymmetric hydrogen-transfer reaction to introduce chirality in dihydro-β- ...