Bioinspired chemical synthesis of monomeric and dimeric stephacidin A congeners
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Summary
It is demonstrated that chemical synthesis can provide important insights into biosynthesis by taking advantage of a direct indole C6 halogenation of the related ketopremalbrancheamide.
- Type
- article
- Published
- 2017-09-18
- Cited by
- 41
- References
- 55
- Access
- Open access
- OpenAlex
- https://openalex.org/W2755773200
- Semantic Scholar
- https://api.semanticscholar.org/CorpusID:205298393
Keywords
Prenylation, Chemistry, Indole test, Biosynthesis, Stereochemistry
References
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- Utilizing DART Mass Spectrometry to Pinpoint Halogenated Metabolites from a Marine Invertebrate-Derived Fungus
- Stephacidin A and B: two structurally novel, selective inhibitors of the testosterone-dependent prostate LNCaP cells.
- Enantioselective synthesis of stephacidin B.
- Fungal Origins of the Bicyclo[2.2.2]diazaoctane Ring System of Prenylated Indole Alkaloids
- Efficacy of a combined oral formulation of derquantel-abamectin against the adult and larval stages of nematodes in sheep, including anthelmintic-resistant strains.
- Synthesis and Bioconversions of Notoamide T: A Biosynthetic Precursor to Stephacidin A and Notoamide B
- Concise, asymmetric, stereocontrolled total synthesis of stephacidins A, B and notoamide B.
- Prenylated indole derivatives from fungi: structure diversity, biological activities, biosynthesis and chemoenzymatic synthesis.
- Synthetic studies towards paraherquamide F: synthesis of the 1,7-dihydropyrano[2,3-g]indole ring system
- Marine natural products: a new wave of drugs?
- Intermolecular and Intramolecular Diels—Alder Cycloadditions of 3-Ylidenepiperazine-2,5-diones and 5-Acycloxy-2(1H)-pyrazinones.
- A new antibiotic CJ-17,665 from Aspergillus ochraceus.
- Enantioselective total synthesis of avrainvillamide and the stephacidins.
- Computational prediction of 1H and 13C chemical shifts: a useful tool for natural product, mechanistic, and synthetic organic chemistry.
Cited by
- OxaD, a versatile indolic nitrone synthase from the marinederived fungus Penicillium oxalicum F30
- Total Syntheses of Stephacidin Congeners
- Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo [2.2.2]diazaoctane ring system from marine and terrestrial fungi
- Asperversiamides, Linearly Fused Prenylated Indole Alkaloids from the Marine-Derived Fungus Aspergillus versicolor.
- Rapid Generation of Molecular Complexity by Chemical Synthesis: Highly Efficient Total Synthesis of Hexacyclic Alkaloid (-)-Chaetominine and Its Biosynthetic Implications.
- Multidirectional desymmetrization of pluripotent building block en route to diastereoselective synthesis of complex nature-inspired scaffolds
- Organoboron chemistry comes to light: recent advances in photoinduced synthetic approaches to organoboron compounds
- A Late-Stage Functionalization Approach to Derivatives of the Pyrano[3,2- a]carbazole Natural Products.
- Synthesis of Functionalized Indole-1-oxide Derivatives via Cascade Reactions of Allenynes and tBuONO.
- Toward efficient photocatalytic pure water splitting for simultaneous H2 and H2O2 production
- Stabilization of Transient 3-Chloroindolenines Enables Diverse Functionalization.
- Construction of Bisindolines via Oxidative Coupling Cyclization.
- Mimicking of Phase I Metabolism Reactions of Molindone by HLM and Photocatalytic Methods with the Use of UHPLC-MS/MS
- Flavin-Dependent Monooxygenases NotI and NotI′ Mediate Spiro-Oxindole Formation in Biosynthesis of the Notoamides
- A unified strategy to reverse-prenylated indole alkaloids: total syntheses of preparaherquamide, premalbrancheamide, and (+)-VM-55599
- 21-Epi-taichunamide D and (±)-versicaline A, three unusual alkaloids from the endophytic Aspergillus versicolor F210
- Stereocontrolled transformations of cyclohexadienone derivatives to access stereochemically rich and natural product-inspired architectures.
- Biosynthetically Inspired Divergent Syntheses of Merocytochalasans
- Recent advances in total syntheses of complex dimeric natural products.
- Base-promoted, CBr4-mediated tandem bromination/intramolecular Friedel-Crafts alkylation of N-aryl enamines: a facile access to 1H- and 3H-indoles.
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