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

Abstract

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 (GlasbyJ. S.GlasbyJ. S.Encyclopedia of the AlkaloidsPlenum PressNew York1975) and Lounasmaa et al.’s review (LounasmaaM.HanhinenP.WestersundM.LounasmaaM.HanhinenP.WestersundM.CordellG. A.The AlkaloidsAcademic PressSan Diego, CA199952103195) as well as clarifies the work of Yunusov et al. (MalikovV. M.SharipovM. R.YunusovS. Yu.MalikovV. M.SharipovM. R.YunusovS. Yu.Khim. Prir. Soedin.19728760761. RakhimovD. A.SharipovM. R.AripovKh. N.MalikovV. M.ShakirovT. T.YunusovS. Yu.RakhimovD. A.SharipovM. R.AripovKh. N.MalikovV. M.ShakirovT. T.YunusovS. Yu.Khim. Prir. Soedin.19706724725). 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.