Synthesis, Absolute Configurations, and Biological Activities of Floral Scent Compounds from Night-Blooming Araceae
- Autor(en)
- Patrick Stamm, Florian Etl, Artur Campos D. Maia, Stefan Dötterl, Stefan Schulz
- Abstrakt
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 α-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.
- Organisation(en)
- Department für Botanik und Biodiversitätsforschung
- Externe Organisation(en)
- Technische Universität Carolo-Wilhelmina zu Braunschweig, Universidade Federal da Paraíba, Paris-Lodron Universität Salzburg
- Journal
- The Journal of Organic Chemistry
- Band
- 86
- Seiten
- 5245-5254
- Anzahl der Seiten
- 10
- ISSN
- 0022-3263
- DOI
- https://doi.org/10.1021/acs.joc.1c00145
- Publikationsdatum
- 2021
- Peer-reviewed
- Ja
- ÖFOS 2012
- 106008 Botanik, 106012 Evolutionsforschung, 106042 Systematische Botanik
- Schlagwörter
- Link zum Portal
- https://ucris.univie.ac.at/portal/de/publications/synthesis-absolute-configurations-and-biological-activities-of-floral-scent-compounds-from-nightblooming-araceae(98258434-fe9a-436c-9c47-878d1b83daf9).html