Macroline indole alkaloids synthesis

Liu, X., Cook, J. M. General Approach for the Synthesis of Sarpagine/Macroline Indole Alkaloids. Enantiospecific Total Synthesis of the Indole Alkaloid Trinervine. Org. Lett. 2001, 3,4023-4026. 

Tran YS, Kwon O (2005) An Application of the Phosphine-Catalyzed [4-1-2] Aimulation in Indole Alkaloid Synthesis Formal Syntheses of (-l-/-)-Alstonerine and (-i-/—)-Macroline. Org Lett 7 4289... 

Synthesis of Sarpagine/Macroline-Related Indole Alkaloids... 

Villalstonine (109) has been partially synthesized (Scheme 32) from its two halves , pleiocarpamine (110) and macroline, in an analogous synthesis, a process which in this case reverses a degradation of the alkaloid. It is interesting to note that the partial synthesis may well procieed via 11), in which electrophilic attack has occurred at the -position of the pleiocarpamine indole nucleus. As in the example discussed earlier (see p. 211) this / -substitution is secured by a subsequent intramolecular nucleophilic addition to the a-carbon, C-2. 

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