Isolation and synthesis of N-(2-methyl-3-oxodec-8-enoyl)-2-pyrroline and 2-(hept-5-enyl)-3-methyl-4-oxo-6,7,8,8a-tetrahydro-4H-pyrrolo(2,1-b)-3-oxazine, two new fungal metabolites with in vivo antijuvenile hormone and insecticidal activity
| Autor: | Cantin Sanz, Angel, Moya Sanz, Mª del Pilar, Castillo López, Mª Ángeles, Primo Millo, Jaime, Miranda Alonso, Miguel Ángel, Primo Yufera, Eduardo |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 1999 |
| Předmět: | |
| Zdroj: | RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia instname |
| DOI: | 10.1002/(sici)1099-0690(199901)1999:1<221::aid-ejoc221>3.0.co;2-y |
| Popis: | [EN] Two new natural products, N-(2-methyl-3-oxodec-8-enoyl)-2-pyrroline (2) and 2-(hept-5-enyl)-3-methyl-4-oxo-6,7,8,8a-tetrahydro-4H-pyrrolo[2,1-b]-1,3-oxazine (3), have been isolated from Penicillium brevicompactum Dierckx. Compound 2 has shown an important in vivo anti-juvenile-hormone (anti-JH) activity while compound 3 has exhibited insecticidal activity against Oncopeltus fasciatus Dallas. Both products have been synthesized starting from 1,4-hexadiene, by means of a sequence of reactions which includes the preparation of 6-octenoic acid and its transformation into the corresponding acid chloride, in order to acylate Meldrum's acid. Subsequent aminolysis with pyrrolidine, followed by methylation at the activated position of the ß-oxo amide with iodomethane, introduction of a methoxy group at the pyrrolidine ring by anodic oxidation and final elimination of methanol on SiO2 led to 2 and 3. The fact that both metabolites can be prepared by the same sequence indicates that they must be biogenetically related. Based on structural similarities, compounds 2 and 3 are also closely related to the recently discovered brevioxime |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|