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Survey of Synthetic Approaches to Natural (Peyssonenynes) and Unnatural Acetoxyenediynes

Identifieur interne : 001578 ( Istex/Curation ); précédent : 001577; suivant : 001579

Survey of Synthetic Approaches to Natural (Peyssonenynes) and Unnatural Acetoxyenediynes

Auteurs : Patricia García-Domínguez ; Rosana Alvarez [Espagne] ; Ángel R. De Lera [Espagne]

Source :

European Journal of Organic Chemistry [ 1434-193X ] ; 2012-09.

RBID : ISTEX:C7FC948F3AA8E591951ADC12AF18D0A9829AFE8E

Descripteurs français

Wicri :
- topic : Anhydride.

English descriptors

KwdEn :
- Ac2o, Acetate, Acetic, Acetic anhydride, Acetoxyenediyne, Acetoxyenediynes, Acetoxyenyne, Acetoxyenynes, Alkyne, Amide, Angew, Anhydride, Anion, Aqueous solution, Brine, Calcd, Carbonate, Cdcl3, Chem, Colorless, Column chromatography, Deprotection, Diyne, Diynyl, Diynyl anion, Dmap, Dropwise, Enol, Enol acetate, Enol acetates, Ester, Et2o, Et3n, Ether, Etoac, Further purification, General procedure, Gmbh, Hexane, Hplc, Hrms, Iodoalkyne, Ipr3si, Isomer, Ketone, Kgaa, Lera, Lett, Lhmds, Lithium, Meoh, Mmol, Model system, Nacl, Natural products, Nbu4nf, Nbuli, Next step, Nh4cl, Organic layers, Palmitic acid, Peyssonenynes, Piperidine, Potassium carbonate, Propargylic, Propargylic ketone, Propargylic ketones, Purification, Reaction mixture, Reagent, Room temperature, Silica, Sonogashira, Tbaf, Terminal alkynes, Tetrahedron, Tetrahedron lett, Title compound, Title product, Tmeda, Unnatural acetoxyenediynes, Unsymmetrical, Verlag, Verlag gmbh, Weinheim, Weinreb, Weinreb amide.
Teeft :
- Ac2o, Acetate, Acetic, Acetic anhydride, Acetoxyenediyne, Acetoxyenediynes, Acetoxyenyne, Acetoxyenynes, Alkyne, Amide, Angew, Anhydride, Anion, Aqueous solution, Brine, Calcd, Carbonate, Cdcl3, Chem, Colorless, Column chromatography, Deprotection, Diyne, Diynyl, Diynyl anion, Dmap, Dropwise, Enol, Enol acetate, Enol acetates, Ester, Et2o, Et3n, Ether, Etoac, Further purification, General procedure, Gmbh, Hexane, Hplc, Hrms, Iodoalkyne, Ipr3si, Isomer, Ketone, Kgaa, Lera, Lett, Lhmds, Lithium, Meoh, Mmol, Model system, Nacl, Natural products, Nbu4nf, Nbuli, Next step, Nh4cl, Organic layers, Palmitic acid, Peyssonenynes, Piperidine, Potassium carbonate, Propargylic, Propargylic ketone, Propargylic ketones, Purification, Reaction mixture, Reagent, Room temperature, Silica, Sonogashira, Tbaf, Terminal alkynes, Tetrahedron, Tetrahedron lett, Title compound, Title product, Tmeda, Unnatural acetoxyenediynes, Unsymmetrical, Verlag, Verlag gmbh, Weinheim, Weinreb, Weinreb amide.

Abstract

Four convergent synthetic approaches to acetoxyenediynes have been explored to gain access to peyssonenynes A and B, which are natural products isolated from the red alga Peyssonelia caulifera. After optimization of the routes with a palmitic acid based model system, the synthesis of the peyssonenynes was completed by using, as the key steps, 1) Ni/Cu co‐catalyzed cross‐coupling of terminal alkynes, 2) Sonogashira cross‐coupling, 3) the addition of a diynyl anion to a Weinreb amide, and 4) the previously reported Cadiot–Chodkiewicz cross‐coupling reaction. Because bulky amide bases stereoselectively provided the (E)‐ and (Z)‐acetoxyenynes from the precursor ynones, the cross‐coupling routes to obtaining the acetoxyenediynes by using these stereochemically homogeneous intermediates are comparable to the alternatives in which enolacetate formation of the acetoxyenediyne motif takes place at a late stage in the synthesis.

Url:

https://api.istex.fr/document/C7FC948F3AA8E591951ADC12AF18D0A9829AFE8E/fulltext/pdf

DOI: 10.1002/ejoc.201200246

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Patricia García-Domínguez

<affiliation><mods:affiliation>Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain, Fax: +34‐986‐818622</mods:affiliation>
<wicri:noCountry code="subField">+34‐986‐818622</wicri:noCountry>
</affiliation>

Le document en format XML

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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Ac2o</term>
<term>Acetate</term>
<term>Acetic</term>
<term>Acetic anhydride</term>
<term>Acetoxyenediyne</term>
<term>Acetoxyenediynes</term>
<term>Acetoxyenyne</term>
<term>Acetoxyenynes</term>
<term>Alkyne</term>
<term>Amide</term>
<term>Angew</term>
<term>Anhydride</term>
<term>Anion</term>
<term>Aqueous solution</term>
<term>Brine</term>
<term>Calcd</term>
<term>Carbonate</term>
<term>Cdcl3</term>
<term>Chem</term>
<term>Colorless</term>
<term>Column chromatography</term>
<term>Deprotection</term>
<term>Diyne</term>
<term>Diynyl</term>
<term>Diynyl anion</term>
<term>Dmap</term>
<term>Dropwise</term>
<term>Enol</term>
<term>Enol acetate</term>
<term>Enol acetates</term>
<term>Ester</term>
<term>Et2o</term>
<term>Et3n</term>
<term>Ether</term>
<term>Etoac</term>
<term>Further purification</term>
<term>General procedure</term>
<term>Gmbh</term>
<term>Hexane</term>
<term>Hplc</term>
<term>Hrms</term>
<term>Iodoalkyne</term>
<term>Ipr3si</term>
<term>Isomer</term>
<term>Ketone</term>
<term>Kgaa</term>
<term>Lera</term>
<term>Lett</term>
<term>Lhmds</term>
<term>Lithium</term>
<term>Meoh</term>
<term>Mmol</term>
<term>Model system</term>
<term>Nacl</term>
<term>Natural products</term>
<term>Nbu4nf</term>
<term>Nbuli</term>
<term>Next step</term>
<term>Nh4cl</term>
<term>Organic layers</term>
<term>Palmitic acid</term>
<term>Peyssonenynes</term>
<term>Piperidine</term>
<term>Potassium carbonate</term>
<term>Propargylic</term>
<term>Propargylic ketone</term>
<term>Propargylic ketones</term>
<term>Purification</term>
<term>Reaction mixture</term>
<term>Reagent</term>
<term>Room temperature</term>
<term>Silica</term>
<term>Sonogashira</term>
<term>Tbaf</term>
<term>Terminal alkynes</term>
<term>Tetrahedron</term>
<term>Tetrahedron lett</term>
<term>Title compound</term>
<term>Title product</term>
<term>Tmeda</term>
<term>Unnatural acetoxyenediynes</term>
<term>Unsymmetrical</term>
<term>Verlag</term>
<term>Verlag gmbh</term>
<term>Weinheim</term>
<term>Weinreb</term>
<term>Weinreb amide</term>
</keywords>
<keywords scheme="Teeft" xml:lang="en"><term>Ac2o</term>
<term>Acetate</term>
<term>Acetic</term>
<term>Acetic anhydride</term>
<term>Acetoxyenediyne</term>
<term>Acetoxyenediynes</term>
<term>Acetoxyenyne</term>
<term>Acetoxyenynes</term>
<term>Alkyne</term>
<term>Amide</term>
<term>Angew</term>
<term>Anhydride</term>
<term>Anion</term>
<term>Aqueous solution</term>
<term>Brine</term>
<term>Calcd</term>
<term>Carbonate</term>
<term>Cdcl3</term>
<term>Chem</term>
<term>Colorless</term>
<term>Column chromatography</term>
<term>Deprotection</term>
<term>Diyne</term>
<term>Diynyl</term>
<term>Diynyl anion</term>
<term>Dmap</term>
<term>Dropwise</term>
<term>Enol</term>
<term>Enol acetate</term>
<term>Enol acetates</term>
<term>Ester</term>
<term>Et2o</term>
<term>Et3n</term>
<term>Ether</term>
<term>Etoac</term>
<term>Further purification</term>
<term>General procedure</term>
<term>Gmbh</term>
<term>Hexane</term>
<term>Hplc</term>
<term>Hrms</term>
<term>Iodoalkyne</term>
<term>Ipr3si</term>
<term>Isomer</term>
<term>Ketone</term>
<term>Kgaa</term>
<term>Lera</term>
<term>Lett</term>
<term>Lhmds</term>
<term>Lithium</term>
<term>Meoh</term>
<term>Mmol</term>
<term>Model system</term>
<term>Nacl</term>
<term>Natural products</term>
<term>Nbu4nf</term>
<term>Nbuli</term>
<term>Next step</term>
<term>Nh4cl</term>
<term>Organic layers</term>
<term>Palmitic acid</term>
<term>Peyssonenynes</term>
<term>Piperidine</term>
<term>Potassium carbonate</term>
<term>Propargylic</term>
<term>Propargylic ketone</term>
<term>Propargylic ketones</term>
<term>Purification</term>
<term>Reaction mixture</term>
<term>Reagent</term>
<term>Room temperature</term>
<term>Silica</term>
<term>Sonogashira</term>
<term>Tbaf</term>
<term>Terminal alkynes</term>
<term>Tetrahedron</term>
<term>Tetrahedron lett</term>
<term>Title compound</term>
<term>Title product</term>
<term>Tmeda</term>
<term>Unnatural acetoxyenediynes</term>
<term>Unsymmetrical</term>
<term>Verlag</term>
<term>Verlag gmbh</term>
<term>Weinheim</term>
<term>Weinreb</term>
<term>Weinreb amide</term>
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<keywords scheme="Wicri" type="topic" xml:lang="fr"><term>Anhydride</term>
</keywords>
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<front><div type="abstract" xml:lang="en">Four convergent synthetic approaches to acetoxyenediynes have been explored to gain access to peyssonenynes A and B, which are natural products isolated from the red alga Peyssonelia caulifera. After optimization of the routes with a palmitic acid based model system, the synthesis of the peyssonenynes was completed by using, as the key steps, 1) Ni/Cu co‐catalyzed cross‐coupling of terminal alkynes, 2) Sonogashira cross‐coupling, 3) the addition of a diynyl anion to a Weinreb amide, and 4) the previously reported Cadiot–Chodkiewicz cross‐coupling reaction. Because bulky amide bases stereoselectively provided the (E)‐ and (Z)‐acetoxyenynes from the precursor ynones, the cross‐coupling routes to obtaining the acetoxyenediynes by using these stereochemically homogeneous intermediates are comparable to the alternatives in which enolacetate formation of the acetoxyenediyne motif takes place at a late stage in the synthesis.</div>
</front>
</TEI>
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Survey of Synthetic Approaches to Natural (Peyssonenynes) and Unnatural Acetoxyenediynes

Survey of Synthetic Approaches to Natural (Peyssonenynes) and Unnatural Acetoxyenediynes

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Descripteurs français

English descriptors

Abstract

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