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Synlett 1996; 1996(7): 612-614
DOI: 10.1055/s-1996-5555
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Highly Functionalised Pyroglutamates by Intramolecular Aldol Reactions: Towards the Pyroglutamate Skeleton of Oxazolomycin

Mark D. Andrews, Andrew G. Brewster, Mark G. Moloney*
  • *Dyson Perrins Laboratory, South Parks Road, Oxford, OX1 3QY, Email: mmoloney@sable.ox.ac.uk
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Publication Date:
31 December 2000 (online)

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Intramolecular aldol reactions of cis-N-acyloxazolidines 6a,b gave protected α-substituted pyroglutamates. The observed stereocontrol arises as a result of the chiral memory of the oxazolidine template, and regioselective enolate formation prior to ring closure. The major products, 10 and 12, have the correct relative stereochemistry for the oxazolomycin group of antitumour antibiotics.

pyroglutamate - intramolecular - cyclization - aldol - oxazolomycin

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