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Ministerio de Universidades - Gobierno de España

Título: STEREODIVERGENT SYNTHESIS OF POLYOXYGENATED CYCLOHEXANES
Autor: Toribio Villarroya, Gladys
Universidad: Universidad Autónoma de Barcelona
Departamento: Quimica
Fecha de Lectura: 15/06/2011
Programa de doctorado: Quimica
Dirección:
- FIGUEREDO GALIMANY, MARTA (DIRECTOR)
- FONT CIERCO, JOSEP (CODIRECTOR)
Tribunal:
- CARREÑO GARCIA, MARIA DEL CARMEN (PRESIDENTE)
- Shafir, Alexandr (SECRETARIO)
- Ortiz Mellet, Carmen (VOCAL)
Descriptores:
- QUIMICA DE PRODUCTOS NATURALES ORGANICOS
Localización: BIBLIOTECA DE COMUNICACIÓN Y HEMEROTECA GENERAL UAB

2011toribstere.pdf

Marcador: https://www.educacion.gob.es/teseo/mostrarRef.do?ref=932901Añadir a favoritos.
Resumen:
1. SUMMARY In this thesis a methodology for the preparation enantiomeric alcohols in multigram scale been established by taking advantage of an enzymatic acetylation to resolve a racemate. These chiral alcohols have been used as starting materials for the synthesis of diverse natural products with potential biological prop First, we dealt with the synthesis of both enantiomers of the 4-hydroxy-2-cyclohexenone and their silyl ethers derivatives in 2-3 in 3 steps and around 55% yield. The practical syntheses developed in our laboratories deliver these compounds in high enantiomeric excesses and good yields. Moreover, the multigram scale preparation favours their use as precursors for the synthesis of more complex molecules with potential biological activity. We also prepared the syntheses of both antipodes of trans-cyclohex-2-ene-1,4-diol and its silyl ether derivatives, which are very important intermediates in the synthesis of organic compounds as well as in polymer chemistry. Their syntheses have been successfully carried out in 65% and 72% yield, respectively, improving the previously published works. On the other hand, both enantiomeric alcohols were our material of choice to undertake a systematic synthesis of gabosines and anhydrogabosines through a sterodivergent strategy involving an oxidation/pyrolysis or a reduction of the C-S bond. The oxidation/pyrolysis pathway (path A) allowed the synthesis of (+)- and (-)-epiepoformin, (+)- and (-)-epoformin and (+) and (-)-gabosine A. Finally, reduction of C-S bond (path B) delivered gabosines B and F.

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