Welwitindolinones, Unusual Alkaloids from the Blue-Green Algae Hapalosiphon welwitschii and Westiella intricata. Relationship to Fischerindoles and Hapalinodoles

Stratmann, Klemens; Moore, Richard E.; Bonjouklian, Rosanne; Deeter, Jack B.; Patterson, Gregory M. L.; Shaffer, Stacey; Smith, Charles D.; Smitka, Tim A.

doi:10.1021/ja00101a015

Cited by 330 publications

(272 citation statements)

References 2 publications

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“…4 and 5). Details of the purification and characterization of these compounds is reported elsewhere (Berry et al, submitted for publication), however, chemical characterization has identified these compounds as belonging to the hapalindoles, a group of indole alkaloids previously identified from Fischerella and related genera (Moore et al, 1984(Moore et al, ,1987Smitka et al, 1992;Stratmann et al, 1994). Although previous work (Moore et al, 1997;Smitka et al, 1992;Doan et al, 2000;Doan et al, 2001) has characterized biological activity of these compounds (e.g.…”

Section: Discussionmentioning

confidence: 99%

The zebrafish (Danio rerio) embryo as a model system for identification and characterization of developmental toxins from marine and freshwater microalgae

Berry

Gantar

Gibbs

et al. 2007

Comparative Biochemistry and Physiology Part C: Toxicology &

109

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The zebrafish (Danio rerio) embryo has emerged as an important model of vertebrate development. As such, this model system is finding utility in the investigation of toxic agents that inhibit, or otherwise interfere with, developmental processes (i.e. developmental toxins), including compounds that have potential relevance to both human and environmental health, as well as biomedicine. Recently, this system has been applied increasingly to the study of microbial toxins, and more specifically, as an aquatic animal model, has been employed to investigate toxins from marine and freshwater microalgae, including those classified among the so-called "harmful algal blooms" (HABs). We have developed this system for identification and characterization of toxins from cyanobacteria (i.e. "blue-green algae") isolated from the Florida Everglades and other freshwater sources in South and Central Florida. Here we review the use of this system as it has been applied generally to the investigation of toxins from marine and freshwater microalgae, and illustrate this utility as we have applied it to the detection, bioassay-guided fractionation and subsequent characterization of developmental toxins from freshwater cyanobacteria.

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Section: Discussionmentioning

confidence: 99%

The zebrafish (Danio rerio) embryo as a model system for identification and characterization of developmental toxins from marine and freshwater microalgae

Berry

Gantar

Gibbs

et al. 2007

Comparative Biochemistry and Physiology Part C: Toxicology &

109

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“…The reaction proceeded cleanly in aqueous ethanol at 120 °C with a catalyst loading of only 2 mol%, delivering 11 in 92% isolated yield. The welwitindolinones are a fascinating group of structurally unique metabolites isolated from blue-green algae that contain 3,4-bridged or spiro-cyclobutaneoxindole moieties [34,35]. Due to their challenging structures and their broad spectrum of biological activities, these compounds have attracted the attention of synthetic chemists for some time, although their complexity has prevented the completion of total syntheses for most of them thus far [36].…”

Section: Preparation Of Complex [Pth{(pme 2 O) 2 H}(pme 2 Oh)] Firstmentioning

confidence: 99%

Synthetic Applications of the Parkins Nitrile Hydration Catalyst [PtH{(PMe2O)2H}(PMe2OH)]: A Review

Cadierno

2015

Applied Sciences

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Abstract:The air-stable hydride-platinum(II) complex [PtH{(PMe2O)2H}(PMe2OH)], reported by Parkins and co-workers in 1995, is the most versatile catalyst currently available for the hydration of C≡N bonds. It features remarkable activity under relatively mild conditions and exceptionally high functional group compatibility, facts that have allowed the implementation of this complex in the synthesis of a large number of structurally complex, biologically active molecules and natural products. In this contribution, synthetic applications of the Parkins catalyst are reviewed.

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“…The formation of the (3S)-diastereomer was noteworthy, as this stereochemistry was found in at least one member of the welwitindolinone family. 71 Interestingly, the mixture of oxime diastereomers ultimately proved inconsequential, since both diastereomers, when subjected to the modified protocol for the Kim et al's oxime rearrangement, 66a,b were converted smoothly to (-)-N-methylwelwitindolinone C isothiocyanate 285.…”

Section: Synthesis Of (-)-N-methylwelwitindolinone C Isothio Cyanatementioning

confidence: 99%

Modern Methods for Total Synthesis of Important Oxindole Alkaloids

Cook¹

2016

Organic Chemistry Insights

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This review describes the latest synthetic methods found in the literature for the construction of complex natural products containing the spiro[pyrrolidine-3,3′-oxindole] ring system and other oxindoles that are closely related. The spirooxindole system is the central structure of many different types of natural products and synthetic drugs, which are associated with various biological activities. The well-known interest that these compounds inspire in academia, as well as in industry together with our efforts toward the total synthesis of sarpagine-/macroline-related oxindoles inspired us to review this topic. Herein, the strategies used by other expert groups in the field of synthetic organic chemistry and their results are presented in a critical way. The examples were selected on the basis of the elegant way chemists resolved their synthetic challenges. Many other excellent syntheses of complex oxindoles can be found in the literature, but were not included due to the limit in the length of this manuscript.KEY WORDS: spirocyclic oxindoles, oxindole alkaloids, alstonia oxindoles, cross coupling reactions, spirocyclic rearrangements, new synthetic methods CITATION: Fonseca and cook. modern methods for total synthesis of important Oxindole alkaloids.

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Welwitindolinones, Unusual Alkaloids from the Blue-Green Algae Hapalosiphon welwitschii and Westiella intricata. Relationship to Fischerindoles and Hapalinodoles

Cited by 330 publications

References 2 publications

The zebrafish (Danio rerio) embryo as a model system for identification and characterization of developmental toxins from marine and freshwater microalgae

The zebrafish (Danio rerio) embryo as a model system for identification and characterization of developmental toxins from marine and freshwater microalgae

Synthetic Applications of the Parkins Nitrile Hydration Catalyst [PtH{(PMe2O)2H}(PMe2OH)]: A Review

Modern Methods for Total Synthesis of Important Oxindole Alkaloids

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