Bio-Inspired Fragmentations: Rapid Assembly of Indolones, 2-Quinolinones, and (-)-Goniomitine

Haokun Li; Peng Cheng; Long Jiang; Jin-Liang Yang; Liansuo Zu

doi:10.1002/anie.201611830

Bio-Inspired Fragmentations: Rapid Assembly of Indolones, 2-Quinolinones, and (-)-Goniomitine

Angew Chem Int Ed Engl. 2017 Mar 1;56(10):2754-2757. doi: 10.1002/anie.201611830. Epub 2017 Jan 27.

Authors

Haokun Li¹, Peng Cheng², Long Jiang¹, Jin-Liang Yang², Liansuo Zu^{1

2}

Affiliations

¹ School of Pharmaceutical Sciences, Tsinghua University, Beijing, 100084, China.
² Collaborative Innovation Center for Biotherapy, West China Medical School, Sichuan University, Chengdu, 610041, China.

PMID: 28128515
DOI: 10.1002/anie.201611830

Abstract

Inspired by the biogenetic origin of goniomitine, new synthetic bio-inspired fragmentation strategies for the synthesis of functionalized 2-quinolinones and indolones have been developed. Remarkable synthetic efficiency was achieved by telescoping several transformations into one-pot reactions, allowing for the direct coupling of 2-alkynyl-anilines and diazo ketones. The synthetic utility was demonstrated by the 5-step asymmetric total synthesis of (-)-goniomitine from 2-ethyl-cyclopentanone.

Keywords: fragmentation; goniomitine; indolones; quinolinones; total synthesis.

Publication types

Research Support, Non-U.S. Gov't