LrgpV1, Istex, Curation, bibRecord, 000647

Synthetic studies towards garsubellin A: synthesis of model systems and potential mimics by regioselective lithiation of bicyclo[3.3.1]nonane-2,4,9-trione derivatives from catechinic acid

Identifieur interne : 000647 ( Istex/Curation ); précédent : 000646; suivant : 000648

Synthetic studies towards garsubellin A: synthesis of model systems and potential mimics by regioselective lithiation of bicyclo[3.3.1]nonane-2,4,9-trione derivatives from catechinic acid

Auteurs : Nadia M. Ahmad [Royaume-Uni] ; Vincent Rodeschini [Royaume-Uni] ; Nigel S. Simpkins [Royaume-Uni] ; Simon E. Ward [Royaume-Uni] ; Claire Wilson [Royaume-Uni]

Source :

Organic & Biomolecular Chemistry [ 1477-0520 ] ; 2007.

RBID : ISTEX:B7DF17E00AEC85F9B1966633ABA866EAB6A765A7

Descripteurs français

Wicri :
- topic : Pétrole.

English descriptors

KwdEn :
- Allyl, Aqueous nacl, Aroch, Aromatic moiety, Biomol, Bridged, Bridged ketone, Bridgehead, Bridgehead position, Bridgehead substitution, Bromide, Carboxylic acid, Catechinic, Catechinic acid, Catechol, Cdcl3, Chcl3, Chcl3 mmax, Chem, Column chromatography, Deep solution, Derivative, Electrophiles, Garsubellin, Hrms, Ketal, Ketone, Lett, Lithiation, Ltmp, Mgso4, Mmax, Mmol, Nacl, Natural products, Organic extracts, Organic layers, Oxidative, Oxidative degradation, Petroleum, Prenyl, Prenyl bromide, Quenched, Reaction mixture, Regioselective lithiation, Royal society, Substituents, Substitution, Tetrahedron lett, Title compound, Total synthesis, Vacuo, Various electrophiles.
Teeft :
- Allyl, Aqueous nacl, Aroch, Aromatic moiety, Biomol, Bridged, Bridged ketone, Bridgehead, Bridgehead position, Bridgehead substitution, Bromide, Carboxylic acid, Catechinic, Catechinic acid, Catechol, Cdcl3, Chcl3, Chcl3 mmax, Chem, Column chromatography, Deep solution, Derivative, Electrophiles, Garsubellin, Hrms, Ketal, Ketone, Lett, Lithiation, Ltmp, Mgso4, Mmax, Mmol, Nacl, Natural products, Organic extracts, Organic layers, Oxidative, Oxidative degradation, Petroleum, Prenyl, Prenyl bromide, Quenched, Reaction mixture, Regioselective lithiation, Royal society, Substituents, Substitution, Tetrahedron lett, Title compound, Total synthesis, Vacuo, Various electrophiles.

Abstract

Bridgehead lithiations have successfully been carried out on substrates derived from catechinic acid, which possess the core bicyclo[3.3.1]nonane-1,3,5-trione structure present in garsubellin A. Using an external quench method, various electrophiles have been incorporated at the C-5 bridgehead position in a one-step process that appears to be sensitive to the substitution pattern on the bicyclic system. Regioselective lithiation at the C-3 sp2 centre was achieved by changing the base used from LDA to LTMP. Following the introduction of a prenyl substituent by bridgehead substitution, annulation of a THF ring, analogous to that in garsubellin A, was possible via an epoxidation–ring opening sequence. Oxidative modification of the catechol substituent of the catechinic acid core was possible to give systems with muconic acid, ortho-quinone or furan 2-carboxylic acid side chains.

Url:

https://api.istex.fr/document/B7DF17E00AEC85F9B1966633ABA866EAB6A765A7/fulltext/pdf

DOI: 10.1039/b704311b

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<term>Aroch</term>
<term>Aromatic moiety</term>
<term>Biomol</term>
<term>Bridged</term>
<term>Bridged ketone</term>
<term>Bridgehead</term>
<term>Bridgehead position</term>
<term>Bridgehead substitution</term>
<term>Bromide</term>
<term>Carboxylic acid</term>
<term>Catechinic</term>
<term>Catechinic acid</term>
<term>Catechol</term>
<term>Cdcl3</term>
<term>Chcl3</term>
<term>Chcl3 mmax</term>
<term>Chem</term>
<term>Column chromatography</term>
<term>Deep solution</term>
<term>Derivative</term>
<term>Electrophiles</term>
<term>Garsubellin</term>
<term>Hrms</term>
<term>Ketal</term>
<term>Ketone</term>
<term>Lett</term>
<term>Lithiation</term>
<term>Ltmp</term>
<term>Mgso4</term>
<term>Mmax</term>
<term>Mmol</term>
<term>Nacl</term>
<term>Natural products</term>
<term>Organic extracts</term>
<term>Organic layers</term>
<term>Oxidative</term>
<term>Oxidative degradation</term>
<term>Petroleum</term>
<term>Prenyl</term>
<term>Prenyl bromide</term>
<term>Quenched</term>
<term>Reaction mixture</term>
<term>Regioselective lithiation</term>
<term>Royal society</term>
<term>Substituents</term>
<term>Substitution</term>
<term>Tetrahedron lett</term>
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<term>Bridged ketone</term>
<term>Bridgehead</term>
<term>Bridgehead position</term>
<term>Bridgehead substitution</term>
<term>Bromide</term>
<term>Carboxylic acid</term>
<term>Catechinic</term>
<term>Catechinic acid</term>
<term>Catechol</term>
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<term>Chcl3 mmax</term>
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<term>Column chromatography</term>
<term>Deep solution</term>
<term>Derivative</term>
<term>Electrophiles</term>
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<term>Hrms</term>
<term>Ketal</term>
<term>Ketone</term>
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<term>Lithiation</term>
<term>Ltmp</term>
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<term>Mmol</term>
<term>Nacl</term>
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<term>Organic layers</term>
<term>Oxidative</term>
<term>Oxidative degradation</term>
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<term>Reaction mixture</term>
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<term>Royal society</term>
<term>Substituents</term>
<term>Substitution</term>
<term>Tetrahedron lett</term>
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<front><div type="abstract">Bridgehead lithiations have successfully been carried out on substrates derived from catechinic acid, which possess the core bicyclo[3.3.1]nonane-1,3,5-trione structure present in garsubellin A. Using an external quench method, various electrophiles have been incorporated at the C-5 bridgehead position in a one-step process that appears to be sensitive to the substitution pattern on the bicyclic system. Regioselective lithiation at the C-3 sp2 centre was achieved by changing the base used from LDA to LTMP. Following the introduction of a prenyl substituent by bridgehead substitution, annulation of a THF ring, analogous to that in garsubellin A, was possible via an epoxidation–ring opening sequence. Oxidative modification of the catechol substituent of the catechinic acid core was possible to give systems with muconic acid, ortho-quinone or furan 2-carboxylic acid side chains.</div>
</front>
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Synthetic studies towards garsubellin A: synthesis of model systems and potential mimics by regioselective lithiation of bicyclo[3.3.1]nonane-2,4,9-trione derivatives from catechinic acid

Synthetic studies towards garsubellin A: synthesis of model systems and potential mimics by regioselective lithiation of bicyclo[3.3.1]nonane-2,4,9-trione derivatives from catechinic acid

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Descripteurs français

English descriptors

Abstract

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