Synthesis of notoamide J: a potentially pivotal intermediate in the biosynthesis of several prenylated indole alkaloids.
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An efficient total synthesis of notoamide J, a new prenylated indole alkaloid and potential biosynthetic precursor, is described herein.Abstract:
An efficient total synthesis of notoamide J, a new prenylated indole alkaloid and potential biosynthetic precursor, is described herein. Starting from l-proline and a substituted tryptophan derivative, this synthesis also employs an oxidation and pinacol rearrangement for the formation of the oxindole in the final step.read more
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Biochemical characterization of NotB as an FAD-dependent oxidase in the biosynthesis of notoamide indole alkaloids.
Shengying Li,Jennifer M. Finefield,James D. Sunderhaus,Timothy J. McAfoos,Robert M. Williams,Robert M. Williams,David H. Sherman +6 more
TL;DR: In vitro characterization of NotB, which catalyzes the indole 2,3-oxidation of notoamide E (13), leading to notoamides C (11) and D (12) through an apparent pinacol-like rearrangement, demonstrates 10 as a pivotal branching point inNotoamide biosynthesis.
References
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Paraherquamides, brevianamides, and asperparalines: laboratory synthesis and biosynthesis. An interim report.
Robert M. Williams,Rhona J. Cox +1 more
TL;DR: Key biosynthetic studies are described, along with classical synthetic approaches as well as those inspired by Nature for the synthesis of these interesting molecules.
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Isolation, Structure Elucidation, and Biomimetic Total Synthesis of Versicolamide B, and the Isolation of Antipodal ()-Stephacidin A and (+)-Notoamide B from Aspergillus versicolor NRRL 35600**
Thomas J. Greshock,Alan W. Grubbs,Ping Jiao,Donald T. Wicklow,Donald T. Wicklow,James B. Gloer,Robert M. Williams +6 more
TL;DR: The isolation, structure elucidation, and confirmatory biomimetic total synthesis of the first member of the paraherquamide-stephacidin family to possess the rare anti-relative stereochemistry within the bicyclo-diazaoctane ring system are described.
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Notoamides A–D: Prenylated Indole Alkaloids Isolated from a Marine‐Derived Fungus, Aspergillus sp.
Hikaru Kato,Takushi Yoshida,Takanori Tokue,Yuka Nojiri,Hiroshi Hirota,Tomihisa Ohta,Robert M. Williams,Robert M. Williams,Sachiko Tsukamoto +8 more
TL;DR: Six new prenylated indole alkaloids, named notoamides F−K (8−13), were isolated from a marine-derived Aspergillus sp.
Journal ArticleDOI
Studies in relation to biosynthesis. XLII. The structural elucidation and some aspects of the biosynthesis of the brevianamides-A and -E.
Arthur J. Birch,J.J. Wright +1 more
TL;DR: In this article, the structural elucidation and biosynthesis of brevianamides-A and -E were discussed, and they were shown to be biogenetically derived from tryptophan, proline and mevalonic acid.
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The structure of paraherquamide, a toxic metabolite from penicillium paraherquei
TL;DR: A new toxic metabolite was isolated from Penicillium paraherquei and the structure was determined by X-ray diffraction analysis as mentioned in this paper, which was designated as paraherquamide.