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J Org Chem


Title:"Synthesis, Absolute Configurations, and Biological Activities of Floral Scent Compounds from Night-Blooming Araceae"
Author(s):Stamm P; Etl F; Maia ACD; Dotterl S; Schulz S;
Address:"Institute of Organic Chemistry, Technische Universitat Braunschweig, Hagenring 30, 38106 Braunschweig, Germany. Department of Botany and Biodiversity Research, University of Vienna, Rennweg 14, 1030 Vienna, Austria. Department of Systematics and Ecology, Federal University of Paraiba, 58051-900 Joao Pessoa, Brazil. Department of Biosciences, Paris-Lodron University of Salzburg, Hellbrunnerstrasse 34, 5020 Salzburg, Austria"
Journal Title:J Org Chem
Year:2021
Volume:20210316
Issue:7
Page Number:5245 - 5254
DOI: 10.1021/acs.joc.1c00145
ISSN/ISBN:1520-6904 (Electronic) 0022-3263 (Linking)
Abstract:"The uncommon jasmone derivatives dehydrojasmone, isojasmol, and isojasmyl acetate, floral scent compounds from night-blooming Araceae, were synthesized in a scalable synthesis employing conjugate addition with a selenoacetal as the key step. The stereoselective strategy with subsequent enzymatic kinetic resolution allowed determining the absolute configuration of the natural compounds by GC on a chiral phase. The homoterpene (E)-4,8-dimethyl-1,3,7-nonatrien-5-yl acetate, another uncommon scent compound, was obtained by alpha-regioselective aldehyde prenylation. The biological activities of dehydrojasmone and isojasmol were investigated in field assays, showing that these unique volatiles are able to selectively attract specific cyclocephaline scarab beetle pollinators"
Keywords:*Araceae Flowers Odorants Pheromones Pollination *Volatile Organic Compounds;
Notes:"MedlineStamm, Patrick Etl, Florian Maia, Artur Campos D Dotterl, Stefan Schulz, Stefan eng 2021/03/17 J Org Chem. 2021 Apr 2; 86(7):5245-5254. doi: 10.1021/acs.joc.1c00145. Epub 2021 Mar 16"

 
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