brevianamide-a has been researched along with paraherquamide* in 2 studies
1 review(s) available for brevianamide-a and paraherquamide
| Article | Year |
|---|---|
Paraherquamides, brevianamides, and asperparalines: laboratory synthesis and biosynthesis. An interim report.
Studies from our laboratories on the paraherquamide, brevianamide, and asperparaline families of natural products are reviewed. It has been proposed that the unique core ring system that is common to this family of compounds arises by a biological intramolecular Diels-Alder cycloaddition reaction. Key biosynthetic studies are described, along with classical synthetic approaches as well as those inspired by Nature for the synthesis of these interesting molecules. Topics: Alkaloids; Cyclization; Fungi; Indolizines; Piperazines; Spiro Compounds | 2003 |
1 other study(ies) available for brevianamide-a and paraherquamide
| Article | Year |
|---|---|
Biomimetic Diels-Alder cyclizations for the construction of the brevianamide, paraherquamide, sclerotamide, asperparaline and VM55599 ring systems.
A potentially bio-mimetic Diels-Alder cyclization to construct the bicyclo[2.2.2] ring system common to the paraherquamides, marcfortines, sclerotamides, brevianamides, VM55599, and asperparaline is reported. Epi-deoxybrevianamide E (22) is converted into the corresponding lactim ether (23) and then oxidized with DDQ to provide an azadiene (24) which is tautomerized in the presence of base to azadiene 25 which, spontaneously cyclizes to give a 2:1 mixture of cycloadducts 26 and 27. These cycloadducts are each in turn, converted into D,L-C-19-epi-brevianamide A (20) and D,L-brevianamide B (6). The stereochemical implications of the [4 + 2] cycloaddition is discussed in the context of a working hypothesis on the biosynthesis of this family, particularly VM55599. Topics: Alkaloids; Anthelmintics; Cyclization; Indolizines; Piperazines; Spiro Compounds; Stereoisomerism | 1998 |