Tesis doctoral de Gladys Toribio Villarroya
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.
Datos académicos de la tesis doctoral «Stereodivergent synthesis of polyoxygenated cyclohexanes«
- Título de la tesis: Stereodivergent synthesis of polyoxygenated cyclohexanes
- Autor: Gladys Toribio Villarroya
- Universidad: Autónoma de barcelona
- Fecha de lectura de la tesis: 15/06/2011
Dirección y tribunal
- Director de la tesis
- Marta Figueredo Galimany
- Tribunal
- Presidente del tribunal: María del carmen Carreño garcia
- carmen Ortiz mellet (vocal)
- (vocal)
- (vocal)