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Synthesis 2010(16): 2816-2822  
DOI: 10.1055/s-0029-1218843
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Short and Efficient Synthesis of (2S,3S,4S)-tert-Butyl 3,4-Dihydroxy-2-(methoxymethyl)-5-oxopyrrolidine-1-carboxylate

Mikko Passiniemi, Ari M. P. Koskinen*
Aalto University, School of Science and Technology, Department of Chemistry, P.O. Box 16100 (Kemistintie 1), 00076 Aalto, Finland
Fax: +358(9)47022538; e-Mail: ari.koskinen@tkk.fi;
Further Information

Publication History

Received 14 April 2010
Publication Date:
25 June 2010 (online)

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Abstract

Asymmetric synthesis of the title compound was accomplished starting from l-serine. Stannoxane-mediated lactamization provided the key intermediate in good yield.

Key words

natural products - stereoselective synthesis - olefination - α,β-unsaturated lactam - dihydroxylation

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