A new approach to neuraminic acid analogues via 1,2-oxazines.
A new stereoselective and potentially very flexible (C(5) + C(3) + C(1)) approach to neuraminic acid derivatives and analogues has been established using enantiopure nitrones and alkoxyallenes as C(3) and C(1) building blocks. Substituent OR(2) in position 4 of neuraminic acid analogues is defined by the alkoxyallene employed for the synthesis of the intermediate 1,2-oxazine. Side chain R(1) can be varied by using different precursor nitrones and introduction of different protection groups R(3) at the amino function is also possible.
Bressel
Bettina
B
Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany.
Reissig
Hans-Ulrich
HU
D015394:Molecular Structure; D009438:Neuraminic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D009438:Neuraminic Acids; D010078:Oxazines