149108-61-2Relevant articles and documents
Regioselective synthesis of 3-(1H-indol-3-yl)-5-(1H-indole-3-carbonyl)-4- hydroxyfuroic acids: Route to hydroxyfuroic acid-based insulin receptor activators
Chou, Shan-Yen,Tsai, Henry J.
, p. 247 - 258 (2012/03/27)
A new class of insulin receptor activator with a hydroxyfuroic acid in place of a hydroxyquinone moiety is reported. The synthesis of 3-(1H-indol-3-yl)-5-(1H-indole-3-carbonyl)-4-hydroxyfuroic acids (26-30) requires seven major steps. Key elements in the syntheses include (1) sequential preparation of two 4-(N-protected indole)-3-methoxy-furoic 2,5-dicarboxylic esters (4 and 6); (2) regioselective conversion of the furoic diacid 8 into its C-5 methyl ester 10 with methyl chloroformate; and (3) acylation of 10 by a 7-substituted indole under a mild condition. This study demonstrates a feasible route of synthesizing insulin receptor activators with a hydroxyfuroic acid scaffold. Among those hydroxyfuroic acid compounds, compound 28 demonstrates insulin receptor activation potential comparable to Merck's compound 2 with a dihydroxybenzoquinone scaffold.
Synthesis of arcyriarubin a and arcyriaflavin a via cross-coupling of indolylboronic acid with dibromomaleimides
Wang, Ke,Liu, Zhanzhu
experimental part, p. 144 - 150 (2010/03/24)
Arcyriarubin A was first isolated by Steglich in 1980; it is also the key intermediate in the synthesis of indolocarbazole compounds. A new synthetic approach to the natural products arcyriaflavin A and arcyriarubin A is described. The key step is a Suzuk
