Total synthesis of pipecolic acid and 1-C-alkyl 1,5-iminopentitol derivatives by way of stereoselective aldol reactions from (S)-isoserinal.
Org Biomol Chem
; 16(7): 1118-1125, 2018 02 14.
Article
de En
| MEDLINE
| ID: mdl-29362764
A short synthesis of iminosugars and pipecolic acid derivatives has been realized through aldol addition of a pyruvate, a range of ketones and (S)-isoserinal, followed by catalytic reductive intramolecular amination. The stereoselective aldol reaction was achieved successfully by using tertiary amines or di-zinc aldol catalysts, thus constituting two parallel routes to optically pure products with good yields and high diastereoselectivities. These carbohydrate analogues may be the inhibitors of potent glycosidases and glycosyltransferases.
Texte intégral:
1
Collection:
01-internacional
Base de données:
MEDLINE
Langue:
En
Journal:
Org Biomol Chem
Sujet du journal:
BIOQUIMICA
/
QUIMICA
Année:
2018
Type de document:
Article
Pays d'affiliation:
Pologne
Pays de publication:
Royaume-Uni