Natural acetylenes. Part XLII. Novel C7, C8, C9, and C10 polyacetylenes from fungal cultures

Hearn, Milton T. W.; Jones, E. R. H.; Pellatt, Martin G.; Thaller, V.; Turner, John L.

doi:10.1039/p19730002785

Cited by 19 publications

(14 citation statements)

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“…Triynes 222 and 223 were isolated from the fungus Poria sinuosa (family Polyporaceae) by Cambie et al170 Despite their unstable structures, Thaller and co‐workers have successfully synthesized the methyl ester analogues of both 222 and 223 through a Cadiot–Chodkiewicz coupling 171. Jones and co‐workers have isolated the triynol 224 from the sheathed woodtuft Kuehneromyces mutabilis (family Strophariaceae), a commonly encountered edible mushroom 172. We have constructed the triyne core of 224 in a similar manner as that of 200 (Scheme ) by using a Fritsch–Buttenberg–Wiechell rearrangement 157.…”

Section: Triynes 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: Triynes From Fungimentioning

confidence: 99%

Synthesis of Naturally Occurring Polyynes

2006

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“…The highly unstable 20 was the first natural C7 polyyne to be identified and was isolated from the fungus Ramaria flava by Jones and coworkers. 20 Scheme…”

Section: Methodology and Model Systemsmentioning

confidence: 99%

“…Jones and coworkers isolated the triynol 21 from the neutral fractions of cultures of the sheathed (or two-toned) woodtuft (Kuehneromyces mutabilis), a very commonly encountered toadstool, as well as from three other fungal sources (Scheme 4). 20 The triyne framework of 21 could be assembled in a manner similar to that used for 20. 21 Reaction of 15 with LiC≡CCH 3 gave alcohol 22 as a colorless oil in quantitative yield.…”

Section: Synthesis Of Naturally Occurring Triynolsmentioning

confidence: 99%

A Divergent Synthesis of Triyne Natural Products and Glycosylated Analogues Using a Carbenoid Rearrangement

Luu¹,

Shi²,

Lowary³

et al. 2005

Synthesis

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Using a carbenoid rearrangement to introduce the conjugated acetylenic framework, a series of triynols has been synthesized in five steps from 1,4-butynediol. Several of the triyne alcohols are known natural products and others are glycosylated analogues. This route avoids the use of terminal diynes as precursors, which can be unstable and/or difficult to prepare. It is therefore procedurally attractive in comparison to more traditional routes such as the Cadiot-Chodkiewicz and Sonogashira coupling reactions.

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“…Ungeachtet der unbeständigen Strukturen gelang Thaller und Mitarbeitern die Synthese der Methylester‐Analoga von 222 und 223 mithilfe einer Cadiot‐Chodkiewicz‐Kupplung 171. Jones et al isolierten das Triinol 224 aus dem Stockschwämmchen ( Kuehneromyces mutabilis ; Strophariaceae ‐Familie), einem weit verbreiteten Speisepilz 172. Wir nutzten zum Aufbau der zentralen Triin‐Einheit in 224 eine ähnliche Fritsch‐Buttenberg‐Wiechell‐Umlagerung wie bei der Synthese von 200 (siehe Schema ) 157.…”

Section: Triine 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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Natural acetylenes. Part XLII. Novel C7, C8, C9, and C10 polyacetylenes from fungal cultures

Abstract: Psatyrella sarcocephala and belongs to the Coprinaceae family. Thus, no polyacetylenes have been reported in the genus Psilocybe, sensu Singer.

Cited by 19 publications

References 0 publications

Synthesis of Naturally Occurring Polyynes

Synthesis of Naturally Occurring Polyynes

A Divergent Synthesis of Triyne Natural Products and Glycosylated Analogues Using a Carbenoid Rearrangement

Synthese von Polyin‐Naturstoffen

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