Stereospecific Total Synthesisof the Indole Alkaloid Ervincidine. Establishment of the C-6Hydroxyl Stereochemistry

摘要

The total synthesis of the indole alkaloid ervincidine (>3) is reported. This research provides a general entry into C-6 hydroxy-substituted indole alkaloids with either an α or a β configuration. This study corrects the errors in Glasby’s book (Glasby J. S.. Encyclopedia of the Alkaloids; Plenum Press: New York, 1975 []) and Lounasmaa et al.’s review (Lounasmaa M.; Hanhinen P.; Westersund M. In The Alkaloids; Cordell G. A., editor. , Ed.; Academic Press: San Diego, CA, 1999; Vol. 52, pp 103–195 []) as well as clarifies the work of Yunusov et al. (Malikov V. M.; Sharipov M. R.; Yunusov S. Yu.Khim. Prir. Soedin. 1972, 8, 760−761 []. Rakhimov D. A.; Sharipov M. R.; Aripov Kh. N.; Malikov V. M.; Shakirov T. T.; Yunusov S. Yu.Khim. Prir. Soedin. 1970, 6, 724–725 []). It establishes the correct absolute configuration of the C-6 hydroxyl function in ervincidine. This serves as a structure proof and corrects the misassigned structure reported in the literature.