(S) y (R) -N-BOC, O-Isopropiliden-Alfa-Metilserinalesutilización como precursores de productos de interés biológico

  1. Sucunza Sáenz, David
Supervised by:
  1. Alberto Avenoza Aznar Director
  2. María del Mar Zurbano Asensio Director

Defence university: Universidad de La Rioja

Fecha de defensa: 09 December 2003

Committee:
  1. José Luis García Ruano Chair
  2. Miguel París Fernández Secretary
  3. Josep Bonjoch Sesé Committee member
  4. José Antonio Mayoral Murillo Committee member
  5. Juan Luis Asensio Alvarez Committee member

Type: Thesis

Abstract

This report describes the behaviour of (S)- and (R)-N-Boc-N,O-isopropylidene-a-methylserinals, a-methyl homologues of the Garner's aldehyde, as chiral building blocks in the synthesis of different optically active organic compounds that contain quaternary carbon atoms. Likewise, we have explored the applications of these compounds in the asymmetric synthesis of several products of considerable importance as several a-methyl-a-amino acids and the 4-epi-L-vancosamina, carbohydrate of different glycopeptide antibiotics. Finally, we have attempted to extend this methodology to all sorts of compounds with a quaternary stereocentre that include an amine group. For this reason, we have developed a new synthetic strategy to achieve different a-substituted serines, starting materials of their respective a-alkyl-(aryl)-serinals.