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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
A new approach to neuraminic acid analogues via 1,2-oxazines
Bettina Bressel1, Hans-Ulrich Reissig
1Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany.
Abstract:
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.
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