Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes
The synthesis and structural determination of two new diterpenylhydroquinones: 2β-acetoxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-diene(1) and 2β-hydroxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-dieneis reported (2). These compounds were obtained by coupling via Electrophilic Arom...
Ausführliche Beschreibung
Autor*in: |
Mauricio Cuellar Fritis [verfasserIn] Joan Villena García [verfasserIn] Luis Espinoza Catalán [verfasserIn] Héctor Carrasco Altamirano [verfasserIn] Alejandro Madrid Villegas [verfasserIn] Karen Catalán Marín [verfasserIn] |
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E-Artikel |
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Sprache: |
Englisch |
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2009 |
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In: Molecules - MDPI AG, 2003, 14(2009), 6, Seite 2181-2194 |
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Übergeordnetes Werk: |
volume:14 ; year:2009 ; number:6 ; pages:2181-2194 |
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DOI / URN: |
10.3390/molecules14062181 |
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Katalog-ID: |
DOAJ038750678 |
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10.3390/molecules14062181 doi (DE-627)DOAJ038750678 (DE-599)DOAJadea006d803440729afe0c9d75980a56 DE-627 ger DE-627 rakwb eng QD241-441 Mauricio Cuellar Fritis verfasserin aut Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes 2009 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The synthesis and structural determination of two new diterpenylhydroquinones: 2β-acetoxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-diene(1) and 2β-hydroxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-dieneis reported (2). These compounds were obtained by coupling via Electrophilic Aromatic Substitution (EAS) of 1,4-hydroquinone with primary or tertiary allyl alcohol derivatives of the natural ent-labdanes 3 and 4. With this new method, the best results were observed when mixtures of the primary alcohol derivatives 5-6 (26% yield of compound 1) and diol derivatives 9-10 (28% yield of compound 2) were used. diterpenyl-hydroquinones synthesis ent-labdanes NMR structural determination Organic chemistry Joan Villena García verfasserin aut Luis Espinoza Catalán verfasserin aut Héctor Carrasco Altamirano verfasserin aut Alejandro Madrid Villegas verfasserin aut Karen Catalán Marín verfasserin aut In Molecules MDPI AG, 2003 14(2009), 6, Seite 2181-2194 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:14 year:2009 number:6 pages:2181-2194 https://doi.org/10.3390/molecules14062181 kostenfrei https://doaj.org/article/adea006d803440729afe0c9d75980a56 kostenfrei http://www.mdpi.com/1420-3049/14/6/2181/ kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 14 2009 6 2181-2194 |
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10.3390/molecules14062181 doi (DE-627)DOAJ038750678 (DE-599)DOAJadea006d803440729afe0c9d75980a56 DE-627 ger DE-627 rakwb eng QD241-441 Mauricio Cuellar Fritis verfasserin aut Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes 2009 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The synthesis and structural determination of two new diterpenylhydroquinones: 2β-acetoxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-diene(1) and 2β-hydroxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-dieneis reported (2). These compounds were obtained by coupling via Electrophilic Aromatic Substitution (EAS) of 1,4-hydroquinone with primary or tertiary allyl alcohol derivatives of the natural ent-labdanes 3 and 4. With this new method, the best results were observed when mixtures of the primary alcohol derivatives 5-6 (26% yield of compound 1) and diol derivatives 9-10 (28% yield of compound 2) were used. diterpenyl-hydroquinones synthesis ent-labdanes NMR structural determination Organic chemistry Joan Villena García verfasserin aut Luis Espinoza Catalán verfasserin aut Héctor Carrasco Altamirano verfasserin aut Alejandro Madrid Villegas verfasserin aut Karen Catalán Marín verfasserin aut In Molecules MDPI AG, 2003 14(2009), 6, Seite 2181-2194 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:14 year:2009 number:6 pages:2181-2194 https://doi.org/10.3390/molecules14062181 kostenfrei https://doaj.org/article/adea006d803440729afe0c9d75980a56 kostenfrei http://www.mdpi.com/1420-3049/14/6/2181/ kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 14 2009 6 2181-2194 |
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10.3390/molecules14062181 doi (DE-627)DOAJ038750678 (DE-599)DOAJadea006d803440729afe0c9d75980a56 DE-627 ger DE-627 rakwb eng QD241-441 Mauricio Cuellar Fritis verfasserin aut Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes 2009 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The synthesis and structural determination of two new diterpenylhydroquinones: 2β-acetoxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-diene(1) and 2β-hydroxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-dieneis reported (2). These compounds were obtained by coupling via Electrophilic Aromatic Substitution (EAS) of 1,4-hydroquinone with primary or tertiary allyl alcohol derivatives of the natural ent-labdanes 3 and 4. With this new method, the best results were observed when mixtures of the primary alcohol derivatives 5-6 (26% yield of compound 1) and diol derivatives 9-10 (28% yield of compound 2) were used. diterpenyl-hydroquinones synthesis ent-labdanes NMR structural determination Organic chemistry Joan Villena García verfasserin aut Luis Espinoza Catalán verfasserin aut Héctor Carrasco Altamirano verfasserin aut Alejandro Madrid Villegas verfasserin aut Karen Catalán Marín verfasserin aut In Molecules MDPI AG, 2003 14(2009), 6, Seite 2181-2194 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:14 year:2009 number:6 pages:2181-2194 https://doi.org/10.3390/molecules14062181 kostenfrei https://doaj.org/article/adea006d803440729afe0c9d75980a56 kostenfrei http://www.mdpi.com/1420-3049/14/6/2181/ kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 14 2009 6 2181-2194 |
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10.3390/molecules14062181 doi (DE-627)DOAJ038750678 (DE-599)DOAJadea006d803440729afe0c9d75980a56 DE-627 ger DE-627 rakwb eng QD241-441 Mauricio Cuellar Fritis verfasserin aut Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes 2009 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The synthesis and structural determination of two new diterpenylhydroquinones: 2β-acetoxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-diene(1) and 2β-hydroxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-dieneis reported (2). These compounds were obtained by coupling via Electrophilic Aromatic Substitution (EAS) of 1,4-hydroquinone with primary or tertiary allyl alcohol derivatives of the natural ent-labdanes 3 and 4. With this new method, the best results were observed when mixtures of the primary alcohol derivatives 5-6 (26% yield of compound 1) and diol derivatives 9-10 (28% yield of compound 2) were used. diterpenyl-hydroquinones synthesis ent-labdanes NMR structural determination Organic chemistry Joan Villena García verfasserin aut Luis Espinoza Catalán verfasserin aut Héctor Carrasco Altamirano verfasserin aut Alejandro Madrid Villegas verfasserin aut Karen Catalán Marín verfasserin aut In Molecules MDPI AG, 2003 14(2009), 6, Seite 2181-2194 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:14 year:2009 number:6 pages:2181-2194 https://doi.org/10.3390/molecules14062181 kostenfrei https://doaj.org/article/adea006d803440729afe0c9d75980a56 kostenfrei http://www.mdpi.com/1420-3049/14/6/2181/ kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 14 2009 6 2181-2194 |
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10.3390/molecules14062181 doi (DE-627)DOAJ038750678 (DE-599)DOAJadea006d803440729afe0c9d75980a56 DE-627 ger DE-627 rakwb eng QD241-441 Mauricio Cuellar Fritis verfasserin aut Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes 2009 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The synthesis and structural determination of two new diterpenylhydroquinones: 2β-acetoxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-diene(1) and 2β-hydroxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-dieneis reported (2). These compounds were obtained by coupling via Electrophilic Aromatic Substitution (EAS) of 1,4-hydroquinone with primary or tertiary allyl alcohol derivatives of the natural ent-labdanes 3 and 4. With this new method, the best results were observed when mixtures of the primary alcohol derivatives 5-6 (26% yield of compound 1) and diol derivatives 9-10 (28% yield of compound 2) were used. diterpenyl-hydroquinones synthesis ent-labdanes NMR structural determination Organic chemistry Joan Villena García verfasserin aut Luis Espinoza Catalán verfasserin aut Héctor Carrasco Altamirano verfasserin aut Alejandro Madrid Villegas verfasserin aut Karen Catalán Marín verfasserin aut In Molecules MDPI AG, 2003 14(2009), 6, Seite 2181-2194 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:14 year:2009 number:6 pages:2181-2194 https://doi.org/10.3390/molecules14062181 kostenfrei https://doaj.org/article/adea006d803440729afe0c9d75980a56 kostenfrei http://www.mdpi.com/1420-3049/14/6/2181/ kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 14 2009 6 2181-2194 |
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Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes |
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The synthesis and structural determination of two new diterpenylhydroquinones: 2β-acetoxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-diene(1) and 2β-hydroxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-dieneis reported (2). These compounds were obtained by coupling via Electrophilic Aromatic Substitution (EAS) of 1,4-hydroquinone with primary or tertiary allyl alcohol derivatives of the natural ent-labdanes 3 and 4. With this new method, the best results were observed when mixtures of the primary alcohol derivatives 5-6 (26% yield of compound 1) and diol derivatives 9-10 (28% yield of compound 2) were used. |
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The synthesis and structural determination of two new diterpenylhydroquinones: 2β-acetoxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-diene(1) and 2β-hydroxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-dieneis reported (2). These compounds were obtained by coupling via Electrophilic Aromatic Substitution (EAS) of 1,4-hydroquinone with primary or tertiary allyl alcohol derivatives of the natural ent-labdanes 3 and 4. With this new method, the best results were observed when mixtures of the primary alcohol derivatives 5-6 (26% yield of compound 1) and diol derivatives 9-10 (28% yield of compound 2) were used. |
abstract_unstemmed |
The synthesis and structural determination of two new diterpenylhydroquinones: 2β-acetoxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-diene(1) and 2β-hydroxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-dieneis reported (2). These compounds were obtained by coupling via Electrophilic Aromatic Substitution (EAS) of 1,4-hydroquinone with primary or tertiary allyl alcohol derivatives of the natural ent-labdanes 3 and 4. With this new method, the best results were observed when mixtures of the primary alcohol derivatives 5-6 (26% yield of compound 1) and diol derivatives 9-10 (28% yield of compound 2) were used. |
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Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes |
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