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

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, allo...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-03, Vol.56 (10), p.2754-2757
Main Authors: Li, Haokun, Cheng, Peng, Jiang, Long, Yang, Jin‐Liang, Zu, Liansuo
Format: Article
Language:English
Subjects:
fragmentation
goniomitine
indolones
Ketones
quinolinones
Synthesis
Telescoping
total synthesis
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Summary: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. The convergent coupling of a 2‐alkynyl‐aniline and an α‐diazo ketone involving N−H insertion, intramolecular Michael addition, fragmentation, and regioselective N‐cyclization enabled the asymmetric total synthesis of (−)‐goniomitine in only 5 steps (4 manipulations) from readily available starting materials.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201611830