ES2127690B1 - Procedimientos de obtencion de (+)-puupehenona a partir de terpenoides biciclicos. - Google Patents

Procedimientos de obtencion de (+)-puupehenona a partir de terpenoides biciclicos.

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Publication number
ES2127690B1
ES2127690B1 ES9601891A ES9601891A ES2127690B1 ES 2127690 B1 ES2127690 B1 ES 2127690B1 ES 9601891 A ES9601891 A ES 9601891A ES 9601891 A ES9601891 A ES 9601891A ES 2127690 B1 ES2127690 B1 ES 2127690B1
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Spain
Prior art keywords
puupehenone
procedures
obtaining
aromatic
terpenoids
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
ES9601891A
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English (en)
Other versions
ES2127690A1 (es
Inventor
Barrero Alejandro Fernandez
Roldan Enriq Alvarez-Manzaneda
Rachid Chahboun
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Universidad de Granada
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Universidad de Granada
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Publication date
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Priority to ES9601891A priority Critical patent/ES2127690B1/es
Publication of ES2127690A1 publication Critical patent/ES2127690A1/es
Application granted granted Critical
Publication of ES2127690B1 publication Critical patent/ES2127690B1/es
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Abstract

Procedimientos de obtención de (+)-puupehenona aterpenoides bicíclicos. La presente invención consiste en sendos procedimientos de síntesis de (4aS,6aR,12aR,12bR) 1,2,3,4,4a,5,6,6a,12a,12b-decahidro-10-hidroxi- 4,4,6a,12b-tetrametil-9H-benzo[a]xanten-9-ona, más conocido como (+)-puupehenona, sustancia con propiedades antibacterianas, antifúngicas e inhibidor de la proteína de transferencia del colesteril éster, a partir de (-)-esclareol y de (-)-drimenol, como precursores terpénicos, y aldehido protocatecuico como precursor aromático. En ambos procedimientos es clave la preparación de 1,2-Di-O- bencil-4-bromo-5-O-tert-butildimetilsililbencenotriol como sintón aromático. La condensación del organolítico derivado de éste con 8 a -Acetoxi-11-drimanal en el primer procedimiento, y con drimenal, en el segundo, permite construir el esqueleto carbonada de puupehenona. Se logra la ciclación estereoselectiva hasta el sistema piránico mediante un proceso de alcoxiselenilación.
ES9601891A 1996-08-02 1996-08-02 Procedimientos de obtencion de (+)-puupehenona a partir de terpenoides biciclicos. Expired - Fee Related ES2127690B1 (es)

Priority Applications (1)

Application Number Priority Date Filing Date Title
ES9601891A ES2127690B1 (es) 1996-08-02 1996-08-02 Procedimientos de obtencion de (+)-puupehenona a partir de terpenoides biciclicos.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES9601891A ES2127690B1 (es) 1996-08-02 1996-08-02 Procedimientos de obtencion de (+)-puupehenona a partir de terpenoides biciclicos.

Publications (2)

Publication Number Publication Date
ES2127690A1 ES2127690A1 (es) 1999-04-16
ES2127690B1 true ES2127690B1 (es) 2000-01-01

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Family Applications (1)

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ES9601891A Expired - Fee Related ES2127690B1 (es) 1996-08-02 1996-08-02 Procedimientos de obtencion de (+)-puupehenona a partir de terpenoides biciclicos.

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7276536B2 (en) 2003-03-17 2007-10-02 Japan Tobacco Inc. Method for increasing the bioavailability of the active form of S-[2-([[1-(2-ethylbutyl)cyclohexyl]carbonyl]amino) phenyl] 2-methylpropanethioate
CN105646431A (zh) * 2016-01-05 2016-06-08 哈尔滨工业大学（威海） 一种海洋天然产物Puupehenone的合成方法

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10314813B2 (en) 2017-04-05 2019-06-11 University Of Central Florida Research Foundation, Inc. Antimicrobial compositions for Clostridium difficile
JP7260912B2 (ja) 2017-05-02 2023-04-19 国立大学法人東北大学 リファガールの類縁体、及びリファガール又はその類縁体を含む多標的キナーゼ阻害剤

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7276536B2 (en) 2003-03-17 2007-10-02 Japan Tobacco Inc. Method for increasing the bioavailability of the active form of S-[2-([[1-(2-ethylbutyl)cyclohexyl]carbonyl]amino) phenyl] 2-methylpropanethioate
CN105646431A (zh) * 2016-01-05 2016-06-08 哈尔滨工业大学（威海） 一种海洋天然产物Puupehenone的合成方法
CN105646431B (zh) * 2016-01-05 2020-03-31 哈尔滨工业大学（威海） 一种海洋天然产物Puupehenone的合成方法

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Publication number Publication date
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