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

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., 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.

本文报道了吲哚生物碱（indole alkaloid）欧文生定（ervincidine，3）的全合成（total synthesis）。本研究为制备具有α或β构型的C-6位羟基取代吲哚生物碱提供了通用方法。本研究纠正了格拉斯比专著（Glasby, J. S. 《生物碱百科全书（Encyclopedia of the Alkaloids）》；普伦出版社（Plenum Press）：纽约，1975年）以及卢纳萨马等人的综述（Lounasmaa, M.; Hanhinen, P.; Westersund, M. 收录于《生物碱（The Alkaloids）》；Cordell, G. A. 主编；学术出版社（Academic Press）：加利福尼亚州圣地亚哥，1999年；第52卷，第103–195页）中的错误，并澄清了尤努索夫等人的研究工作（Malikov, V. M.; Sharipov, M. R.; Yunusov, S. Yu. 《天然化合物化学（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. 《天然化合物化学（Khim. Prir. Soedin.）》，1970, 6, 724–725）。本研究确立了欧文生定中C-6位羟基官能团的正确绝对构型，该工作为结构确证提供了依据，并纠正了文献中已报道的错误指定的结构。