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A new stereoselective and potentially very flexible (C5+ C3+ C1) approach to neuraminic acid derivatives and analogues has been established using enantiopure nitrones and alkoxyallenes as C3and C1building blocks. Substituent OR2in position 4 of neuraminic acid analogues is defined by the alkoxyallene employed for the synthesis of the intermediate 1,2-oxazine. Side chain R1can be varied by using different precursor nitrones and introduction of different protection groups R3at the amino function is also possible. [ABSTRACT FROM AUTHOR]

As master craftsmen, modern synthetic chemists are challenged to achieve remarkable feats of efficiency and elegance toward molecular targets. The nature of this pursuit necessitates the collection of synthetic repertoires that are tried and true. With methodologies and pathways increasingly scrutinized, the adept chemist must seek out propitious tools to incorporate into the arsenal. With this in mind, this Account highlights the versatility of alkoxyallenes as precursors to valuable heterocyclic building blocks for such efforts as natural product synthesis. [ABSTRACT FROM AUTHOR]