Beilstein J. Org. Chem.2023,19, 167–175, doi:10.3762/bjoc.19.16
amorph-4-ene-10β-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; chiralgas
chromatography; enantioselective synthesis; GC/MS; semiochemicals; Introduction
Hyperolius cinnamomeoventris (Figure 1) is one of the largest species of reed frogs (Hyperoliidae), which are commonly found in Africa, south of the Sahara. Males of the Hyperoliidae possess a characteristic yellow gular patch on
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Graphical Abstract
Figure 1:
Calling male Hyperolius cinnamomeoventris with exposed vocal sac carrying the yellow gular gland. Figure 1 ...
Beilstein J. Org. Chem.2016,12, 2731–2738, doi:10.3762/bjoc.12.269
, is usually not possible from an EI mass spectrum. In the article, we present the synthesis and for the first time elucidate the structure of macrolides from the frog family Hyperoliidae.
Keywords: chemical communication; chiralgaschromatography; macrocyclic lactones; ring-closing metathesis
natural compound, the other enantiomer (S)-1 was needed as well. It was synthesized according to the synthesis shown in Scheme 2, starting from (S)-propylene oxide instead of the (R)-enantiomer 13. The stereochemistry was determined by chiralgaschromatography as shown in Figure 4. The coinjection of
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Graphical Abstract
Figure 1:
Macrolactones produced in scent glands of frogs: (Z)-Tetradec-5-en-13-olide (1) or (Z)-tetradec-9-e...