Total syntheses of five indole alkaloids from the marine bryozoan Flustra foliacea.
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.
Morales-Ríos
M S
MS
Departamento de Química del Centro de Investigación y de Estudios Avanzados, Instituto Politéctico Nacional, Apartado 14-740, México D. F., 07000 Mexico.
Suárez-Castillo
O R
OR
Trujillo-Serrato
J J
JJ
Joseph-Nathan
P
P
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D007211:Indoles / Q000737:chemistry*; D007448:Invertebrates / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry / Q000379:methods; D015394:Molecular Structure
D000470:Alkaloids; D007211:Indoles