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]1,3-oxazine – Two New Fungal Metabolites with in vivo Anti-Juvenile-Hormone and Insecticidal Activity
✍ Scribed by Ángel Cantín; Pilar Moya; Maria-Angeles Castillo; Jaime Primo; Miguel A. Miranda; Eduardo Primo-Yúfera
- Publisher
- John Wiley and Sons
- Year
- 1999
- Tongue
- English
- Weight
- 132 KB
- Volume
- 1999
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
Two new natural products, N- (2-methyl-3-oxodec-8-enoyl)corresponding acid chloride, in order to acylate Meldrum's acid. Subsequent aminolysis with pyrrolidine, followed by 2-pyrroline (2) and 2-(hept-5-enyl)-3-methyl-4-oxo-6,7,8,8atetrahydro-4H-pyrrolo[2,1-b]-1,3-oxazine (3), have been methylation at the activated position of the β-oxo amide with iodomethane, introduction of a methoxy group at the isolated from Penicillium brevicompactum Dierckx. Compound 2 has shown an important in vivo anti-juvenile-pyrrolidine ring by anodic oxidation and final elimination of methanol on SiO 2 led to 2 and 3. The fact that both hormone (anti-JH) activity while compound 3 has exhibited insecticidal activity against Oncopeltus fasciatus Dallas. Both metabolites can be prepared by the same sequence indicates that they must be biogenetically related. Based on structural products have been synthesized starting from 1,4-hexadiene, by means of a sequence of reactions which includes the similarities, compounds 2 and 3 are also closely related to the recently discovered brevioxime (1). preparation of 6-octenoic acid and its transformation into the [a] Instituto de Tecnologı ´a Quı ´mica UPV-CSIC, Universidad Poliand alternative synthesis of two new natural products (2 te ´cnica de Valencia, Avenida de los Naranjos s/n, Apartado 22012, E-46022 Valenand 3) from P. brevicompactum, with high in vivo anti-JH cia, Spain