Synthesis of (.+-.)-catharanthine,(+)-anhydrovinblastine, and (-)-anhydrovincovaline

S Raucher, BL Bray, RF Lawrence

Index: Raucher, Stanley; Bray, Brian L.; Lawrence, Ross F. Journal of the American Chemical Society, 1987 ,  vol. 109,  # 2  p. 442 - 446

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Citation Number: 71

Abstract

Abstract: An efficient total synthesis of (*)-catharanthine (1) has been accomplished. Diels- Alder reaction of 8 with a-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/H20 with a 450-W Hanovia mercury lamp through a Pyrex filter provided 14. Reduction of 14 by treatment ...