Bioactive bromopyrrole metabolites from the Caribbean sponge Agelas conifera [Erratum to document cited in CA114(19):182417u]

Keifer, Paul A.; Schwartz, Robert E.; Koker, Moustapha E. S.; Hughes, Robert G.; Rittschof, Dan; Rinehart, Kenneth L.

doi:10.1021/jo00023a055

Cited by 17 publications

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“…It was believed that this oxidation occurs in Nature to make all of these natural products, and that there would be a thermodynamic bias for them to undergo similar transformations in the laboratory. It is worth noting that several other biosynthetic hypotheses have been published by other groups, ,,,,,, and that our hypothesis builds on pioneering work by Rinehart and Horne. , The oxidation of C20 is a strategic disconnection: by saving the oxidation of C20 for the ultimate or penultimate step of the synthesis, the stability and reactivity problems associated with a hemiaminal could be avoided during the majority of the skeleton-building steps. As alluded to earlier, this disconnection was notably lacking in precedent, and thus its inclusion into the retrosynthesis was not without a significant amount of risk.…”

Section: Resultsmentioning

confidence: 87%

Enantioselective Total Syntheses of (−)-Palau’amine, (−)-Axinellamines, and (−)-Massadines

et al. 2011

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Dimeric pyrrole-imidazole alkaloids represent a rich and topologically unique class of marine natural products. This full account will follow the progression of efforts that culminated in the enantioselective total syntheses of the most structurally ornate members of this family: the axinellamines, the massadines, and palau’amine. A bio-inspired approach capitalizing on the pseudo-symmetry of the members of this class is recounted, delivering a deschloro derivative of the natural product core. Next, the enantioselective synthesis of the chlorocyclopentane core featuring a scalable, catalytic, enantioselective Diels–Alder reaction of a 1-siloxydiene is outlined in detail. Finally, the successful divergent conversion of this core to each of the aforementioned natural products, and the ensuing methodological developments are described.

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Section: Resultsmentioning

confidence: 87%

Enantioselective Total Syntheses of (−)-Palau’amine, (−)-Axinellamines, and (−)-Massadines

et al. 2011

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Die Jagd auf Palau'amin

et al. 2007

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Seit der Entdeckung im Jahr 1993 hat Palau'amin die Naturstoffchemiker fasziniert. Seine ungewöhnliche Molekülstruktur und die beschriebene biologische Aktivität machen diesen marinen Naturstoff zu einem lohnenden Ziel für die organische Synthese. Im Laufe der Jahre und im Zusammenhang mit der Isolierung verwandter mariner Alkaloide wurde die postulierte chemische Struktur von Palau'amin angezweifelt, und vor kurzem wurde die relative Konfiguration von Palau'amin schließlich revidiert. Dieser Kurzaufsatz gibt eine sorgfältige Übersicht über die Strukturrevision und deren Bedeutung für die Biosynthese sowie die Totalsynthese.

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The Pursuit of Palau'amine

et al. 2007

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Since its discovery in 1993, the marine natural product palau'amine has intrigued natural product chemists. Its exotic molecular architecture and purported bioactivity made it an ideal target for synthesis. However, as the years went by and related marine alkaloids were isolated, a skeptical eye was cast on the structure of palau'amine; recently these suspicions were confirmed and the structure of palau'amine revised. This Minireview gives a careful overview of the structural revision and its ramifications to both its biogenesis and total synthesis.

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Bioactive bromopyrrole metabolites from the Caribbean sponge Agelas conifera [Erratum to document cited in CA114(19):182417u]

Cited by 17 publications

References 0 publications

Enantioselective Total Syntheses of (−)-Palau’amine, (−)-Axinellamines, and (−)-Massadines

Enantioselective Total Syntheses of (−)-Palau’amine, (−)-Axinellamines, and (−)-Massadines

Die Jagd auf Palau'amin

The Pursuit of Palau'amine

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