Morales-Ríos M S, Suárez-Castillo O R, Trujillo-Serrato J J, Joseph-Nathan P
Departamento de Química del Centro de Investigación y de Estudios Avanzados, Instituto Politéctico Nacional, Apartado 14-740, México D. F., 07000 Mexico.
J Org Chem. 2001 Feb 23;66(4):1186-92. doi: 10.1021/jo0012647.
A general, efficient, and conceptually new approach to the total syntheses of marine-derived indole alkaloids, including (+/-)-flustramines A (1) and B (2), (+/-)-flustramides A (3) and B (4), and (+/-)-debromoflustramine B (5), is outlined. The key step in the syntheses involves the conjugated addition of an organomagnesium species derived from prenyl bromide to 2-hydroxyindolenines. Compounds 1, 2, and 5 have been synthesized in five steps with 23%, 17%, and 16% overall yield, respectively, whereas flustramides 3 and 4 have been synthesized in only four steps with 24% and 18% overall yield, respectively, on the basis of 2-hydroxyindolenines.
