The Journal of Organic Chemistry

Electrochemical oxidation of proline derivatives: total syntheses of bulgecinine and bulgecin C

AGM Barrett, D Pilipauskas

文献索引：Barrett, Anthony G. M.; Pilipauskas, Daniel Journal of Organic Chemistry, 1991 , vol. 56, # 8 p. 2787 - 2800

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被引用次数: 62

摘要

The influence of structure on the efficiency of the electrochemical C-5 oxidation of (2S, 4S)- hydroxyproline carbamate esters is presented. Optimum methoxylation was observed with (2S, 4S)-4-acetoxy-l, 2-pyrrolidine-dicarboxylic acid 2-methyl 1-(2-(trimethylsilyl) ethyl) ester (19). The corresponding C-5 methoxy derivative 20 was converted into bulgecinine (4) via a stereospecific radical homologation to incorporate the C-5 hydroxymethyl substituent. ...