Ungewöhnliche Pulvinsäure‐Dimere aus Kartoffelbovist (<i>Scleroderma citrinum</i>) und Pfefferröhrling (<i>Chalciporus piperatus</i>)

Winner, Monika; Giménez, Alberto; Schmidt, H.; Sontag, Bernd; Steffan, Bert; Steglich, Wölfgang

doi:10.1002/ange.200352529

Cited by 4 publications

(2 citation statements)

References 25 publications

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“…Recently, Snyder and co‐workers reported the first total synthesis of chalcitrin ( 45 ), a structurally distinct pulvinic acid dimer isolated from Calciporous piperatus (Scheme ). The polycyclic core was assembled via Au(I)‐catalyzed Conia ene reaction and NHC‐catalyzed benzoin cyclization.…”

Section: Synthetic Applicationsmentioning

confidence: 99%

Advances in N‐Heterocyclic Carbene Catalysis for Natural Product Synthesis

Que

2020

Eur J Org Chem

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Section: Synthetic Applicationsmentioning

confidence: 99%

Advances in N‐Heterocyclic Carbene Catalysis for Natural Product Synthesis

Que

2020

Eur J Org Chem

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“…Der Pfefferröhrling zeichnet sich durch sein kräftig zitronengelbes Fleisch aus (Abbildung 6). Der chemische Hintergrund des intensiven Gelbs sind neben den bekannten Xerocomsäure ( 4 ) und Norbadion A ( 14 ) die Farbstoffe Sclerocitrin ( 15 ) und Chalcitrin ( 16 ) [14]. Obwohl deren Strukturen sich “nur” von unterschiedlichen Dimeren der Xerocomsäure ableiten, kann man die Komplexheit der zentralen Ringsysteme von 15 und 16 nur bestaunen.…”

Section: Pilzragoutunclassified

Pilzragout nach Chemiker Art

Roth

2015

Chemie in nserer Zeit

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pilZe alS SyntheSeKünStler ein enzym für alle Fälle Fruchtkörper von Ständerpilzen werden häufig Opfer von gefräßigen Insektenlarven. Dagegen verteidigen sie sich durch die Bildung von bioaktiven Substanzen. Hierzu gehören zwei unterschiedlich lange, verzweigtkettige Polyene, die der Schichtpilz BY1 als Reaktion auf eine Verletzung herstellt. Katalysiert wird ihre Synthese über eine einzige, neu entdeckte Polyketid synthase, die dabei acht bzw. neun Doppelbindungen verschieben muss.

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Bioinspired Synthesis of Pulvinic Acids Including Xerocomic Acid and Fluorescence Properties of Bis‐lactone Intermediates

et al. 2023

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A set of representative pulvinic acids were synthesised using a bioinspired strategy. Terphenyl‐quinones (polyporic acid scaffold) were prepared via sequential Suzuki‐Miyaura couplings allowing access to unsymmetrically substituted derivatives in a one‐pot protocol. Subjected to the action of acetic anhydride and DMSO, quinones were converted into bis‐lactone intermediates. Methanolysis and deprotection achieved the total syntheses of the corresponding pulvinic acids. Following this general strategy, symmetrical pulvinic, atromentic, variegatic acids and unsymmetrical congener pinastric, iso‐pinastric, xerocomic and iso‐xerocomic acids were prepared in fair yields. Fluorescence properties were observed for the bis‐lactone intermediates and, as a complement to this synthetic work, optical properties were measured, and fluorescence quantum yields were determined for the bis‐lactone pigments.

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Ungewöhnliche Pulvinsäure‐Dimere aus Kartoffelbovist (Scleroderma citrinum) und Pfefferröhrling (Chalciporus piperatus)

Cited by 4 publications

References 25 publications

Advances in N‐Heterocyclic Carbene Catalysis for Natural Product Synthesis

Advances in N‐Heterocyclic Carbene Catalysis for Natural Product Synthesis

Pilzragout nach Chemiker Art

Bioinspired Synthesis of Pulvinic Acids Including Xerocomic Acid and Fluorescence Properties of Bis‐lactone Intermediates

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