Limno-CP: A Natural-Product-Inspired 5-Aryl-3(2H)-furanone as Scaffold for a Library of alpha-Modified Enones

Amslinger, Sabine and Lindner, Simon K. (2011) Limno-CP: A Natural-Product-Inspired 5-Aryl-3(2H)-furanone as Scaffold for a Library of alpha-Modified Enones. SYNTHESIS-STUTTGART (16). pp. 2671-2683. ISSN 0039-7881, 1437-210X

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Abstract

A library of 5-aryl-3(2H)-furanones that are modified in the alpha-position of the alpha,beta-unsaturated carbonyl system was prepared via simple one-to three-step transformations from one common scaffold. The C-13 NMR characterization of the enone system showed a strong influence of the alpha-substituents, especially on the shifts of the alpha- and beta-carbon atoms. Probing the addition chemistry of nucleophiles versus our alpha-modified enones, a 1,2-addition-elimination was found, but no 1,4-addition.

Item Type: Article
Uncontrolled Keywords: NITRIC-OXIDE PRODUCTION; VINYLIC FLUORINE DISPLACEMENT; URSANE TRITERPENOIDS; SYNTHETIC OLEANANE; CARBONYL-COMPOUNDS; MOUSE MACROPHAGES; DOMINO REACTION; 3(2H)-FURANONES; INHIBITORS; DERIVATIVES; furanones; substituent effects; enones; spiro compounds; 1,2-addition-elimination
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Dr. Sabine Amslinger
Depositing User: Dr. Gernot Deinzer
Date Deposited: 03 Jun 2020 08:55
Last Modified: 03 Jun 2020 08:55
URI: https://pred.uni-regensburg.de/id/eprint/20465

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