77612-52-3Relevant academic research and scientific papers
Synthesis of (+/-)-Catharanthine, (+)-Anhydrovinblastine, and (-)-Anhydrovincovaline
Raucher, Stanley,Bray, Brian L.,Lawrence, Ross F.
, p. 442 - 446 (2007/10/02)
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.
INTRAMOLECULAR HYDRIDE TRANSFER AND CYCLIZATION OF 5-OXO-Na-TOSYL-14,21-DEHYDROSECODINE
Raucher, Stanley,Lawrence, Ross F.
, p. 3731 - 3736 (2007/10/02)
5-Oxo-Na-tosyl-14,21-dehydrosecodine (8) was prepared by bromination of 6 followed by double dehydrobromination with ethyl aluminum dichloride in HMPA.When a dilute solution of 8 was heated, 10 was formed via intramolecular hydride transfer and cyclization.
