Catharanthine C16 substituent effects on the biomimetic coupling with vindoline: preparation and evaluation of a key series of vinblastine analogues

A Tam, H Gotoh, WM Robertson, DL Boger

文献索引：Tam, Annie; Gotoh, Hiroaki; Robertson, William M.; Boger, Dale L. Bioorganic and Medicinal Chemistry Letters, 2010 , vol. 20, # 22 p. 6408 - 6410

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被引用次数: 25

摘要

The examination of the catharanthine C16 substituent effects on the Fe (III)-promoted biomimetic coupling reaction with vindoline is detailed, confirming the importance of the presence of a C16 electron-withdrawing substituent, and establishing an unanticipated unique role (> 10-fold) that the C16 methyl ester plays in the expression of the natural product properties. Thus, replacement of the vinblastine C16′ methyl ester with an ethyl ...