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, 106042 Systematische Botanik, 106012 Evolutionsforschung
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