A Diamino Alcohol Catalyzed Enantioselective Crossed Aldol Reaction of Acetaldehyde with Isatins – A Concise Total Synthesis of Antitumor Agents

Ummareddy Venkata Subba Reddy, Madhu Chennapuram, Kento Seki, Chigusa Seki, Bheemreddy Anusha, Eunsang Kwon, Yuko Okuyama, Koji Uwai, Michio Tokiwa, Mitsuhiro Takeshita, Hiroto Nakano

研究成果: Article査読

12 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)3874-3885
ページ数12
ジャーナルEuropean Journal of Organic Chemistry
2017
26
DOI
出版ステータスPublished - 2017 7 17

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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