Efficient Total Synthesis of Dysidenin, Dysidin, and Barbamide

Ilardi, Elizabeth A.; Zakarian, Armen

doi:10.1002/asia.201100338

Cited by 33 publications

(16 citation statements)

References 27 publications

(30 reference statements)

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“…Such a conservative substitution has previously been observed in other NRPS biosynthetic systems (Figure 3—figure supplement 3 [ 3 ]) (Flatt et al, 2006). This exchange of amino acids gives rise to a new molecular entity; however, it is reminiscent of related compounds, such as dysidin, which was isolated from the cyanobacteria-harboring sponge Dysidea herbacea (Ilardi and Zakarian, 2011). …”

Section: Resultsmentioning

confidence: 99%

Digitizing mass spectrometry data to explore the chemical diversity and distribution of marine cyanobacteria and algae

Luzzatto-Knaan

Garg

Wang

et al. 2017

eLife

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Natural product screening programs have uncovered molecules from diverse natural sources with various biological activities and unique structures. However, much is yet underexplored and additional information is hidden in these exceptional collections. We applied untargeted mass spectrometry approaches to capture the chemical space and dispersal patterns of metabolites from an in-house library of marine cyanobacterial and algal collections. Remarkably, 86% of the metabolomics signals detected were not found in other available datasets of similar nature, supporting the hypothesis that marine cyanobacteria and algae possess distinctive metabolomes. The data were plotted onto a world map representing eight major sampling sites, and revealed potential geographic locations with high chemical diversity. We demonstrate the use of these inventories as a tool to explore the diversity and distribution of natural products. Finally, we utilized this tool to guide the isolation of a new cyclic lipopeptide, yuvalamide A, from a marine cyanobacterium.DOI: http://dx.doi.org/10.7554/eLife.24214.001

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Section: Resultsmentioning

confidence: 99%

Digitizing mass spectrometry data to explore the chemical diversity and distribution of marine cyanobacteria and algae

Luzzatto-Knaan

Garg

Wang

et al. 2017

eLife

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“…Good yields (73–86%) and selectivity (87% to >95%) were observed, validating this approach for the synthesis of amino acid derivatives with sulfinimine auxiliaries. A similar reaction was used in the total synthesis of marine peptides neodysidenin, dysidenin, and dysidin . Rhodium-catalyzed addition of (2,2-dimethylvinyl)trifluoroborate 6 - 7 to indole-derived tert -butanesulfinimine 6 - 6 was used as a key transformation in the synthesis of Penicillum aurantiovirens alkaloid (−)-aurantioclavine (Scheme b) .…”

Section: Addition To the Carbon–nitrogen Double Bondmentioning

confidence: 99%

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

et al. 2016

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The main objective of this review is to provide a comprehensive survey of methods used for stereoselective construction of carbon-nitrogen bonds during the total synthesis of nitrogen-containing natural products that have appeared in the literature since 2000. The material is organized by specific reaction in order of decreasing number of applications in natural product synthesis. About 800 total syntheses of natural products with stereogenic carbon-nitrogen bonds described since 2000 have been reviewed.

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“…286 A highly efficient, diastereoselective ruthenium-catalyzed radical chloroalkylation reaction has been developed for the stereoselective introduction of the di-and trichloromethyl groups found in natural products. 287 The strategy has been successful demonstrated in the concise total synthesis of barbamide 433 and dysidenin 434, a modied hexachlorinated tripeptide isolated from the sponge Dysidea herbacea. An organocatalytic transfer hydrogenation process has been devised for asymmetric synthesis of 4,4-dichloro-3methylbutaldehyde 435.…”

Section: Phytoalexinsmentioning

confidence: 99%

Muscarine, imidaozle, oxazole and thiazole alkaloids

Jin

2013

Nat. Prod. Rep.

132

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Covering: July 2010 to June 2012. Previous review: Nat. Prod. Rep., 2011, 28, 1143-1191. Structurally diverse alkaloids containing five-membered heterocyclic subunits, such as imidazole, oxazole, thiazole, as well as their saturated congeners, are widely distributed in terrestrial and marine organisms and microorganisms. These naturally occurring secondary metabolites often exhibit extensive and pharmacologically important biological activities. The latest progress involving isolation, biological activities, chemical synthetic studies, and biosynthetic pathways of these natural products has been summarized in this review.

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Efficient Total Synthesis of Dysidenin, Dysidin, and Barbamide

Abstract: The total syntheses of three trichloroleucine‐derived marine natural products—dysidenin, dysidin, and barbamide—capitalized on a practical and highly diastereoselective ruthenium catalyzed radical chloroalkylation of N‐acyloxazolidinones as the key step.

Cited by 33 publications

References 27 publications

Digitizing mass spectrometry data to explore the chemical diversity and distribution of marine cyanobacteria and algae

Digitizing mass spectrometry data to explore the chemical diversity and distribution of marine cyanobacteria and algae

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

Muscarine, imidaozle, oxazole and thiazole alkaloids

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