- Sulfinimine-mediated asymmetric synthesis of (R)-(4-methoxy-3,5-dihydroxyphenyl)glycine: The central amino acid of vancomycin and related agents
-
The sulfinimine asymmetric Strecker synthesis, the addition of ethyl aluminum cyano alkoxide, 'EtAl(OR)CN' to sulfinimine 10, has been applied to a concise highly efficient four-step enantioselective synthesis of (R)-(4-methoxy-3,5-dihydroxyphenyl)glycine (3) and its derivatives in >97% ee. These epimerization-sensitive arylglycines are precursors of the key central amino acid of vancomycin and related glycopeptide antibiotics.
- Davis, Franklin A.,Fanelli, Dean L.
-
p. 1981 - 1985
(2007/10/03)
-
- Expeditious syntheses of two arylglycine derivatives corresponding to the central amino acid of the vancomycin family of antibiotics
-
Two expeditious and efficient syntheses (in 7 and 4 steps, respectively) are described for the central amino acid part of the vancomycin family. The first method constitutes a concise asymmetric synthesis, starting from 4- hydroxyphenylacetic acid, of (R)-(3,5-dihydroxy-4-methoxyphenyl)glycine derivatives using Evans' asymmetric azidation methodology. In the second approach, an efficient synthesis of a protected 3,5-dichloro-4- methoxyphenylglycine derivative is described, starting from commercially available (R)-4-hydroxyphenylglycine. These two syntheses are much shorter and operationally simpler than those previously described, and are currently employed in an effort towards the construction of the bicyclic system of vancomycin and ristocetin.
- Pearson, Anthony J.,Chelliah, Mariappan V.,Bignan, Gilles C.
-
p. 536 - 540
(2007/10/03)
-