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Paper | Regular issue | Vol 71, No. 7, 2007, pp.1539-1551
Published online, 27th April, 2007
DOI: 10.3987/COM-07-11048
■ First Total Synthesis of (±)-Flustraminol B

Oscar R. Suárez-Castillo,* Maricruz Sánchez-Zavala, Myriam Meléndez-Rodríguez, Eliazar Aquino-Torres, Martha S. Morales-Ríos, and Pedro Joseph-Nathan

*Centro de Investigaciones Químicas, Universidad A. del Estado de Hidalgo, Apartado 1-328, Pachuca, Hidalgo, 42001, Mexico

Abstract

A first route for the synthesis of a 6-brominated marine alkaloid, flustraminol B (1), is reported using 2,6-dibromoindole (3b) as a key starting material. Bromine atoms were introduced regioselectively to 2b using NBS. The crucial selective reductive cyclization of the corresponding 6-brominated-2,3-dioxindole (7b) was successfully controlled using Red-Al® in toluene, leading to 6-brominated pyrroloindole (8), which by selective N-methylation gave flustraminol B (1).