New synthetic route to granulatimide and its structural analogues.
The Stille coupling reaction of stannylindole 12 with 4-iodoimidazole 13 (or 24) in the presence of PdCl(2)(PPh(3))(2) gave the corresponding indole-imidazole coupling product 14 (or 25), thereby affording a new synthetic approach to the alkaloid granulatimide (7), isolated from the Brazilian ascidian Didemnum granulatum, as well as its structural analogues, 10-methylgranulatimide (23), 17-methylgranulatimide (30), 10,17-dimethylgranulatimide (31).
Yoshida
Takuji
T
Showa Pharmaceutical University, Machida, Tokyo, Japan.
Nishiyachi
Masakazu
M
Nakashima
Nobuyuki
N
Murase
Masayuki
M
Kotani
Eiichi
E
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry; D007211:Indoles / Q000737:chemistry; D008968:Molecular Conformation
D000470:Alkaloids; D007093:Imidazoles; D007211:Indoles; C433587:granulatimide; C029899:imidazole; C030374:indole