A mild synthesis of 1,3-diynes

Kende, Andrew S.; Smith, C.

doi:10.1021/jo00246a057

Cited by 83 publications

(40 citation statements)

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“…Sistodiolynne ( 187 ), a polyketide metabolite of the wood rot decay fungus Sistotrema raduloides , was first isolated by Ayer and co‐workers 146. Sugahara and Ogasawara147 constructed the 1,3‐butadiyne unit of sistodiolynne by using a mild protocol developed by Kende and Smith 148. Coupling of terminal alkyne 188 with ( Z )‐dichloroethene followed by formation of a silyl ether gave 189 .…”

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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“…13 C NMR (100 MHz, CDCl 3 ): δ = 130.0 (ClH C =C), 111.3 (ClHC= C ), 92.4 (C≡C), 91.2 (C≡C), 75.1 [ C H(OCH 2 CH 3 ) 2 ], 61.3 (O C H 2 CH 3 ), 15.0 (OCH 2 C H 3 ) ppm. The spectroscopic data correspond to the literature 18…”

Section: Methodsmentioning

confidence: 68%

“…Finally it was determined that working under an inert atmosphere in dry toluene as solvent, using the Pd‐EnCat TM TPP30 together with a catalytic amount of copper(I) iodide the desired enynes could be generated in reasonable yields (Table 5, Entries 2–4) 17. Under these conditions the cis ‐1,2‐dichloroethylene was more reactive than the trans ‐isomer 18…”

Section: Resultsmentioning

confidence: 99%

Pd‐EnCat^TM TPP30 as a Catalyst for the Generation of Highly Functionalized Aryl‐ and Alkenyl‐Substituted Acetylenes via Microwave‐Assisted Sonogashira Type Reactions

et al. 2009

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We report a rapid microwave‐assisted Sonogashira cross‐coupling of aryl iodides and bromides with terminal alkynes using Pd‐EnCatTM TPP30. Both electron‐rich and electron‐deficient aryl halides reacted smoothly with a broad variety of terminal alkynes in MeCN at 100–120 °C. The coupling products were obtained in good to excellent yields and in high purity. This reaction can be performed under copper‐ and DMF‐free conditions and does not require an inert atmosphere. Furthermore, the encapsulated catalyst can be recovered and recycled by a simple filtration of the reaction mixture. It can be reused in further reactions with only minor decrease in activity. Additionally, we were able to produce a variety of enyne derivatives under modified conditions employing the same Pd‐EnCatTM source. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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“…Sistodiolynne ( 187 ), ein Polyketidmetabolit des Holzfäulepilzes Sistotrema raduloides , wurde erstmals von Ayer et al isoliert 146. Sugahara und Ogasawara147 erhielten die 1,3‐Butadiin‐Einheit von Sistodiolynne unter milden Bedingungen nach einem Verfahren von Kende und Smith 148. Kupplung des terminalen Alkins 188 mit ( Z )‐Dichlorethen und Silylether‐Bildung ergab 189 , das durch TBAF‐vermittelte Dehydrochlorierung und Desilylierung in das sehr unbeständige Produkt 187 umgewandelt wurde (Schema ).…”

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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A mild synthesis of 1,3-diynes

Cited by 83 publications

References 0 publications

Synthesis of Naturally Occurring Polyynes

Synthesis of Naturally Occurring Polyynes

Pd‐EnCat^TM TPP30 as a Catalyst for the Generation of Highly Functionalized Aryl‐ and Alkenyl‐Substituted Acetylenes via Microwave‐Assisted Sonogashira Type Reactions

Synthese von Polyin‐Naturstoffen

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A mild synthesis of 1,3-diynes

Cited by 83 publications

References 0 publications

Synthesis of Naturally Occurring Polyynes

Synthesis of Naturally Occurring Polyynes

Pd‐EnCatTM TPP30 as a Catalyst for the Generation of Highly Functionalized Aryl‐ and Alkenyl‐Substituted Acetylenes via Microwave‐Assisted Sonogashira Type Reactions

Synthese von Polyin‐Naturstoffen

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Product

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Pd‐EnCat^TM TPP30 as a Catalyst for the Generation of Highly Functionalized Aryl‐ and Alkenyl‐Substituted Acetylenes via Microwave‐Assisted Sonogashira Type Reactions