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

[Image: see text] 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 ( J. S. GlasbyEncyclopedia of the Alkaloids; Plenum Press: New York, 1975) and Lounasmaa et al.’s review ( M. Lounasmaa; P. Hanhinen; M. Westersund In The Alkaloids; G. A. Cordell, Ed.; Academic Press: San Diego, CA, 1999; Vol. 52, pp 103–195) as well as clarifies the work of Yunusov et al. ( V. M. Malikov; M. R. Sharipov; S. Yu. YunusovKhim. Prir. Soedin.1972, 8, 760−761. D. A. Rakhimov; M. R. Sharipov; Kh. N. Aripov; V. M. Malikov; T. T. Shakirov; S. Yu. YunusovKhim. 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.