Total synthesis of marine sponge bis(indole) alkaloids of the topsentin class.
The synthesis of four natural bis(indole) alkaloids of topsentin class 1 and 2 is described. Their bis(indole) alpha-carbonylimidazoline and subsequently bis(indole) alpha-carbonylimidazole moieties have been built via the condensation between indolic alpha-ketothioimidate salts 4 and 1-(indol-3'-yl)-1,2-diaminoethane 3. This compound results from the beta-amino indolic hydroxylamine 5 by a two-step sequence. This is the first total synthesis of compounds 1d, 2a, and 2b.
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; D000588:Amines / Q000737:chemistry; D000818:Animals; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000145:classification*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000145:classification*; D015394:Molecular Structure; D009792:Oceans and Seas; D011161:Porifera / Q000737:chemistry*
D000470:Alkaloids; D000588:Amines; D007093:Imidazoles; D007211:Indoles; C070184:topsentin