783. Chemistry of the higher fungi. Part XVI. Polyacetylenic metabolites from Aleurodiscus roseus

Cambie, R. C.; Hirschberg, A.; Jones, E. R. H.; Lowe, G.

doi:10.1039/jr9630004120

Cited by 32 publications

(18 citation statements)

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“…The allenediyne (−)‐marasin ((−)‐ 164 ) was the first naturally occurring allene to be isolated, and was extracted from the culture fluid of Marasmius ramealis in 1959 by Bendz as the active antibiotic component against Staphylococcus aureus 137. The other enantiomer, (+)‐marasin, was later isolated from a different fungal source ( Aleurodiscus roseus ) and appeared to have similar antibiotic activity 138. The highly unsaturated and reactive framework of 164 made it a challenging synthetic target.…”

Section: Diynes From Fungimentioning

confidence: 99%

Synthesis of Naturally Occurring Polyynes

2006

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Over the past fifty years, hundreds of polyyne compounds have been isolated from nature. These often unstable molecules are found in sources as common as garden vegetables and as obscure as bacterial cultures. Naturally occurring polyynes feature a wide range of structural diversity and display an equally broad array of biological properties. Early synthetic efforts relied primarily on Cu-catalyzed, oxidative acetylenic homo- and heterocoupling reactions to assemble the polyyne framework. The past 25 years, however, have witnessed a renaissance in the field of polyyne natural product synthesis: transition-metal-catalyzed alkynylation reactions and asymmetric transformations have combined to substantially expand access to natural polyynes. This Review recounts these synthetic achievements and also highlights both the natural source(s) and biological relevance for many of these compounds.

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Section: Diynes From Fungimentioning

confidence: 99%

Synthesis of Naturally Occurring Polyynes

2006

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“…Bendz extrahierte dieses gegen Staphylococcus aureus wirkende Antibiotikum aus der Kulturbrühe von Marasmius ramealis 137. Das Enantiomer (+)‐Marasin wurde später aus einem anderen Pilz ( Aleurodiscus roseus ) isoliert und zeigt eine ähnliche antibiotische Wirkung 138. Wegen seines hoch ungesättigten und wenig beständigen Gerüsts stellte 164 hohe Anforderungen an eine erfolgreiche Synthese.…”

Section: Diine Aus Pilzenunclassified

Synthese von Polyin‐Naturstoffen

Shun

Tykwinski

2006

Angewandte Chemie

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In den vergangenen fünfzig Jahren wurden Hunderte von Polyinen aus natürlichen Proben isoliert. Diese oftmals unbeständigen Verbindungen finden sich gleichsam in alltäglichen Quellen wie Gartengemüse und weniger geläufigen Quellen wie Bakterienkulturen. Die Strukturen von natürlichen Polyinen unterscheiden sich sehr stark, und entsprechend vielfältig sind die biologischen Eigenschaften dieser Naturstoffe. Frühe Syntheseansätze nutzten zum Aufbau des Polyin‐Gerüsts vorzugsweise die kupferkatalysierte oxidative Homo‐ und Heterokupplung von Alkinen. Eine Renaissance der Polyin‐Naturstoffsynthese hat in den vergangenen 25 Jahren jedoch innovative Synthesetechniken hervorgebracht: Übergangsmetallkatalysierte Alkinylierungen und asymmetrische Umwandlungen haben das Repertoire der Polyin‐Naturstoffsynthese merklich erweitert. Der Aufsatz stellt diese Verbesserungen vor und geht auf die natürliche(n) Quelle(n) und die biologische Bedeutung vieler Substanzen ein.

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“…The first described polyacetylene, biformin or biformyne (7), an epoxytriynol, was isolated from Polyporus biformis in 1947 [5]; its relative configuration was assigned by Anchel and Cohen in 1954 [6] and by Jones and co-workers in 1963 [7] (Scheme 5.2). Further polyacetylenes from Basidiomycete fungi were described later on, in the forms of the epoxytriynol 8 [8], the C 2 -symmetric diepoxydiynediol 9 ((+)-repandiol) [9], the epoxydiynol 10 (nitidon) [10], the diastereoisomeric diynetriols 11 [11] and 12 [12], and the diynetetrol 13 [13]. The unusual (chlorovinyl group) enediynetriol 14 was extracted from a Hyphomycete fungus [14].…”

Section: 2mentioning

confidence: 99%

“…Hydroxylated oligoacetylenes undergo base-catalyzed 5-exo-dig cyclizations to afford 2-ethylidene-oxolanes [7,[11][12][13]249], this reaction having been used for determination of the absolute configurations of oligoacetylenes. Treatment of 11 with aqueous NaOH gave the diyne-enol ether 213 (Scheme 5.47; configuration of the double bond not determined, but probably Z as in 214, 216, and 217).…”

Section: Alkynol Cycloisomerizationmentioning

confidence: 99%