| Title: | "Identification and determination of the absolute configuration of amorph-4-en-10beta-ol, a cadinol-type sesquiterpene from the scent glands of the African reed frog Hyperolius cinnamomeoventris" |
| Author(s): | Ladwig A; Kroll M; Schulz S; |
| Address: | "Institute of Organic Chemistry, Technische Universitat Braunschweig, Hagenring 30, 38106 Braunschweig, Germany. ROR: https://ror.org/010nsgg66. ISNI: https://www.isni.org/isni/0000000110900254" |
| ISSN/ISBN: | 1860-5397 (Print) 1860-5397 (Electronic) 1860-5397 (Linking) |
| Abstract: | "Hyperolid reed frogs are one of the few families of Anurans known to possess glands that emit volatile compounds used in chemical communication. Hyperolius cinnamomeoventris, a model species, possesses a gular gland on its vocal sac that emits chemicals, and sends visual and auditory signals during calling. Previous investigations have shown that the glandular compounds are typically macrocyclic lactones. However, in this work, we show that another major constituent of the male specific gland is (10R,1S,6R,7R,10R)-amorph-4-ene-10beta-ol [(1R,4R,4aR,8aS)-4-isopropyl-1,6-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-ol]. This compound was synthesized for the first time and has the opposite configuration to amorph-4-ene-10beta-ol known from plants. A short synthesis using an organocatalytic approach through a tandem Mannich/intramolecular Diels-Alder reaction led to a mixture of cadinols, which was used for the assignment of the natural cadinol structures and their stereoisomers" |
| Keywords: | Anura Gc/ms chiral gas chromatography enantioselective synthesis semiochemicals; |
| Notes: | "PubMed-not-MEDLINELadwig, Angelique Kroll, Markus Schulz, Stefan eng Germany 2023/02/24 Beilstein J Org Chem. 2023 Feb 16; 19:167-175. doi: 10.3762/bjoc.19.16. eCollection 2023" |
