Total syntheses of brominated marine sponge alkaloids.
Total syntheses of six brominated marine sponge bis(indole) alkaloids of the hamacanthin, spongotine, and topsentin classes are described. Retrosynthetic analysis shows that their structures all include the 1-(6'-bromoindol-3'-yl)-1,2-diaminoethane unit 13a. This key moiety has been prepared from brominated indolic N-hydroxylamine 5b via synthetic intermediate 8b.
Guinchard
Xavier
X
Département de Chimie Moléculaire (SERCO), UMR-5250, ICMG FR-2607, CNRS, Université Joseph Fourier, BP-53, 38041 Grenoble Cedex 9, France.
Vallée
Yannick
Y
Denis
Jean-Noël
JN
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D000818:Animals; D001966:Bromine / Q000737:chemistry*; D015394:Molecular Structure; D009792:Oceans and Seas; D011161:Porifera / Q000737:chemistry*
D000470:Alkaloids; D001966:Bromine