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Bio‐Inspired Fragmentations: Rapid Assembly of Indolones, 2‐Quinolinones, and (−)‐Goniomitine
Author(s) -
Li Haokun,
Cheng Peng,
Jiang Long,
Yang JinLiang,
Zu Liansuo
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201611830
Subject(s) - diazo , chemistry , combinatorial chemistry , fragmentation (computing) , cyclopentanone , stereochemistry , organic chemistry , computer science , catalysis , programming language
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.