Identifizierung von Intermediaten der PR‐Toxin‐Biosynthese durch <i>Penicillium roqueforti</i>

The Robinson annulation is a significant reaction for the synthesis of α,β‐unsaturated ketone ring including the generation of two C−C bonds. It involves a Michael addition of a ketone and a methyl or ethyl vinyl ketone with subsequent intramolecular aldol condensation. Natural products and their structurally related analogues have historically made a major contribution to pharmacotherapy, particularly for cancer and infectious diseases. The Robinson annulation has frequently been employed as a vital step in the total synthesis of these important naturally occurring compounds and related complex biologically active products. In this review, we try to underscore the applications of the Robinson annulation in the total synthesis of biologically active natural products.

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Robinson Annulation Applied to the Total Synthesis of Natural Products

Heravi

Alipour

Zadsirjan

et al. 2023

Asian J Org Chem

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Mechanistische Studien an zwei bakteriellen Diterpencyclasen: Spiroviolen‐Synthase und Tsukubadien‐Synthase

et al. 2017

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Die Mechanismen von zwei Diterpencyclasen aus Streptomyceten – eine mit unbekanntem Produkt, das als der spirocyclische Kohlenwasserstoff Spiroviolen identifiziert wurde, und eine mit dem bekannten Produkt Tsukubadien – wurden detailliert durch Isotopenmarkierungsexperimente untersucht. Obwohl die Strukturen der Produkte sehr unterschiedlich sind, beginnen die Cyclisierungsmechanismen beider Enzyme mit derselben Cyclisierungsreaktion, bevor sie auf dem Weg zu ihren individuellen Produkten divergieren. Dies spiegelt die nahe phylogenetische Verwandtschaft der Enzyme wider.

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Mechanistic Investigations of Two Bacterial Diterpene Cyclases: Spiroviolene Synthase and Tsukubadiene Synthase

et al. 2017

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The mechanisms of two diterpene cyclases from streptomycetes-one with an unknown product that was identified as the spirocyclic hydrocarbon spiroviolene and one with the known product tsukubadiene-were investigated in detail by isotope labeling experiments. Although the structures of the products were very different, the cyclization mechanisms of both enzymes proceed through the same initial cyclization reactions, before they diverge towards the individual products, which is reflected in the close phylogenetic relationship of the enzymes.

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Identifizierung von Intermediaten der PR‐Toxin‐Biosynthese durch Penicillium roqueforti

Cited by 5 publications

References 32 publications

Robinson Annulation Applied to the Total Synthesis of Natural Products

Robinson Annulation Applied to the Total Synthesis of Natural Products

Mechanistische Studien an zwei bakteriellen Diterpencyclasen: Spiroviolen‐Synthase und Tsukubadien‐Synthase

Mechanistic Investigations of Two Bacterial Diterpene Cyclases: Spiroviolene Synthase and Tsukubadiene Synthase

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