Title: | "Identification and Synthesis of Luteolide, a Highly Branched Macrolide Semiochemical from the Mantellid Frog Gephyromantis luteus" |
Author(s): | Melnik K; Menke M; Rakotoarison A; Vences M; Schulz S; |
Address: | "Technische Universitat Braunschweig , Institute of Organic Chemistry , Hagenring 30 , 38106 Braunschweig , Germany. Technische Universitat Braunschweig , Zoological Institute , Mendelssohnstrasse 4 , 38106 Braunschweig , Germany. Zoologie et Biodiversite Animale , Universite d'Antananarivo , BP 906 , Antananarivo 101 , Madagascar" |
DOI: | 10.1021/acs.orglett.9b00852 |
ISSN/ISBN: | 1523-7052 (Electronic) 1523-7052 (Linking) |
Abstract: | "Luteolide is a 10-membered aliphatic macrolactone, (4 R,8 S,9 S)-4,8-dimethylundecan-9-olide ((-) -17), released by the femoral gland of males of the mantellid frog Gephyromantis luteus. Its structure was established using NMR, MS, and chiral GC and confirmed by stereoselective synthesis of different stereoisomers. Among the approximately 20 current macrolides known from the Mantellidae, luteolide is the first example of a volatile macrolide furnishing three stereogenic centers and an ethyl side chain" |
Keywords: | Animals Anura Catalysis Macrolides/*chemical synthesis/*isolation & purification Male Molecular Structure Oxidation-Reduction Pheromones/*chemical synthesis/*isolation & purification Stereoisomerism Volatile Organic Compounds/*chemical synthesis/*isolatio; |
Notes: | "MedlineMelnik, Kristina Menke, Markus Rakotoarison, Andolalao Vences, Miguel Schulz, Stefan eng Research Support, Non-U.S. Gov't 2019/04/05 Org Lett. 2019 Apr 19; 21(8):2851-2854. doi: 10.1021/acs.orglett.9b00852. Epub 2019 Apr 4" |