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Biomimetic total synthesis of malbrancheamide and malbrancheamide B. 2008

Kenneth A Miller, and Timothy R Welch, and Thomas J Greshock, and Yousong Ding, and David H Sherman, and Robert M Williams
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523-1872, USA.

The biomimetic total syntheses of both malbrancheamide and malbrancheamide B are reported. The synthesis of the two monochloro species enabled the structure of malbrancheamide B to be unambiguously assigned. The syntheses each feature an intramolecular Diels-Alder reaction of a 5-hydroxypyrazin-2(1H)-one to construct the bicyclo[2.2.2]diazaoctane core, which has also been proposed as the biosynthetic route to these compounds.

UI MeSH Term Description Entries
D010084 Oxidation-Reduction A chemical reaction in which an electron is transferred from one molecule to another. The electron-donating molecule is the reducing agent or reductant; the electron-accepting molecule is the oxidizing agent or oxidant. Reducing and oxidizing agents function as conjugate reductant-oxidant pairs or redox pairs (Lehninger, Principles of Biochemistry, 1982, p471). Redox,Oxidation Reduction
D006576 Heterocyclic Compounds, 4 or More Rings A class of heterocyclic compounds that include four or more fused rings. Both aromatic or non-aromatic ring structures are included in this category. Heterocyclic Compounds with 4 or More Rings,Five Ring Heterocyclic Compounds,Four Ring Heterocyclic Compounds,Fused Heterocyclic Compounds, Five-Ring,Fused Heterocyclic Compounds, Four-Ring,Heterocyclic Compounds with Four or More Rings,Heterocyclic Compounds, 4-Ring,Heterocyclic Compounds, 5-Ring,Heterocyclic Cpds, 4 Ring,Heterocyclic Cpds, 4 or More Rings,Heterocyclic Cpds, 5 Ring,4-Ring Heterocyclic Compounds,5-Ring Heterocyclic Compounds,Fused Heterocyclic Compounds, Five Ring,Fused Heterocyclic Compounds, Four Ring,Heterocyclic Compounds, 4 Ring,Heterocyclic Compounds, 5 Ring
D000577 Amides Organic compounds containing the -CO-NH2 radical. Amides are derived from acids by replacement of -OH by -NH2 or from ammonia by the replacement of H by an acyl group. (From Grant & Hackh's Chemical Dictionary, 5th ed) Amide
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D026121 Indole Alkaloids Group of alkaloids containing a benzylpyrrole group (derived from TRYPTOPHAN). Indole Alkaloid,Alkaloid, Indole,Alkaloids, Indole
D032701 Biomimetics An interdisciplinary field in materials science, ENGINEERING, and BIOLOGY, studying the use of biological principles for synthesis or fabrication of BIOMIMETIC MATERIALS. Mimetics, Biological,Bio-inspired Engineering,Biomimicry Engineering,Biomimicry Science,Bio inspired Engineering,Bio-inspired Engineerings,Biological Mimetic,Biological Mimetics,Biomimetic,Biomimicry Engineerings,Biomimicry Sciences,Engineering, Bio-inspired,Engineering, Biomimicry,Engineerings, Bio-inspired,Engineerings, Biomimicry,Mimetic, Biological,Science, Biomimicry,Sciences, Biomimicry

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