Enantioselective Total Synthesis of Wieland??Gumlich Aldehyde and (−)??Strychnine

…, J Bonjoch, S García??Rubio, E Peidró…

Index: Sole, Daniel; Bonjoch, Josep; Garcia-Rubio, Silvina; Peidro, Emma; Bosch, Joan Angewandte Chemie - International Edition, 1999 , vol. 38, # 3 p. 395 - 397

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Citation Number: 49

Abstract

Abstract A total synthesis of (−)-strychnine in 15 steps from 1, 3-cyclohexanedione in 0.15% overall yield is described. The sequence followed in the assembling of rings is: E→ AE [2-(2- nitrophenyl)-1, 3-cyclohexanedione]→ ACE (3a-aryloctahydroindol-4-one)→ ACDE (arylazatricyclic core)→ ABCDE (strychnan skeleton)→ ABCDEF (Wieland-Gumlich aldehyde)→ ABCDEFG (strychnine). The key steps of the synthesis are the ...