908332-38-7Relevant academic research and scientific papers
A Diamino Alcohol Catalyzed Enantioselective Crossed Aldol Reaction of Acetaldehyde with Isatins – A Concise Total Synthesis of Antitumor Agents
Subba Reddy, Ummareddy Venkata,Chennapuram, Madhu,Seki, Kento,Seki, Chigusa,Anusha, Bheemreddy,Kwon, Eunsang,Okuyama, Yuko,Uwai, Koji,Tokiwa, Michio,Takeshita, Mitsuhiro,Nakano, Hiroto
, p. 3874 - 3885 (2017/07/22)
Enantioselective crossed aldol reactions of isatin derivatives and acetaldehyde have been developed with a series of simple diamino alcohol catalysts to afford 3-substituted 3-hydroxyindolin-2-ones in high chemical yields (up to 95 %) and optical purities (up to 92 % ee). The synthetic potential of the present protocol has been demonstrated by concise, enantioselective, protecting-group-free, and transition metal-free total syntheses of antitumor and antiviral agents with the tryptanthrin architecture, that is, phaitanthrin B and cephalanthrin A, along with the biologically active indolidine alkaloids chimonamidine and donaxaridine as well as the formal synthesis of CPC-1. The highly enantioselective outcome of this catalytic crossed aldol reaction was evaluated by calculating the Gibbs free energies of the possible transition states.
Silyl-enolization-asymmetric Claisen rearrangement of 2-allyloxyindolin-3-one: enantioselective total synthesis of 3a-hydroxypyrrolo[2,3-b]indoline alkaloid alline
Kawasaki, Tomomi,Takamiya, Wataru,Okamoto, Naoki,Nagaoka, Miyuki,Hirayama, Tetsuya
, p. 5379 - 5382 (2007/10/03)
Asymmetric Claisen rearrangement triggered by silyl-enolization of 2-(1′-nonel-3′-yloxy)indolin-3-ones was performed in order to prepare 3-(2′-nonenyl)-3-hydroxyindolin-2-ones. Total synthesis of 3-hydroxypyrrolo[2,3-b]indoline alkaloid, (+)-alline was ac
