Synthesis of (+/-)-Catharanthine, (+)-Anhydrovinblastine, and (-)-Anhydrovincovaline

Article abstract of DOI:10.1021/ja00236a023

An efficient total synthesis of (+/-)-catharanthine (1) has been accomplished.Diels-Alder reaction of 8 with α-chloroacryloyl chloride followed by reaction with MeOH gave 9.Treatment of 9 with Me3SiI gave 10, and reaction of 10 with indole-3-acetyl chloride provided 11, which was converted to 13.Irradiation of 13 in CH3CN/H2O with a 450-W Hanovia mercury lamp through a Pyrex filter provided 14.Reduction of 14 by treatment with Et3OBF4 and NaBH3CN gave (+/-)-catharanthine (1).The coupling of synthetic (+/-)-catharanthine with natural (-)-vindoline (2) via modified Polonovski reaction provided (+)-anhydrovinblastine (15a) and (-)-anhydrvincovaline (17a), which could be easily separated by flash chromatography.