Approaches to the synthesis of (2R,3S)-2-hydroxymethylpyrrolidin-3-ol (CYB-3) and its C(3) epimer: a cautionary tale

Alison N. Hulme; Karen S. Curley

doi:10.1039/B200415A

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Approaches to the synthesis of (2R,3S)-2-hydroxymethylpyrrolidin-3-ol (CYB-3) and its C(3) epimer: a cautionary tale

Alison N. Hulme*^a and Karen S. Curley^a

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^a Department of Chemistry, The University of Edinburgh, Kings Buildings, West Mains Road, Edinburgh, UK

Abstract

The syntheses of (2R,3S)-2-tert-butyldiphenylsilyloxymethylpyrrolidin-3-ol (TBDPS-protected CYB-3) (21) and its C(3) epimer (25) have been achieved in 9 and 8 steps respectively from D-serine. However, chiral HPLC analysis of the key β-hydroxy ester intermediates in these syntheses (17 and 18) revealed that appreciable levels of racemisation had occurred in the aldol and Claisen condensation reactions used in this synthetic sequence.

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DOI: https://doi.org/10.1039/B200415A
Article type: Paper
Submitted: 14 Jan 2002
Accepted: 22 Feb 2002
First published: 26 Mar 2002

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J. Chem. Soc., Perkin Trans. 1, 2002, 1083-1091

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Approaches to the synthesis of (2R,3S)-2-hydroxymethylpyrrolidin-3-ol (CYB-3) and its C(3) epimer: a cautionary tale

A. N. Hulme and K. S. Curley, J. Chem. Soc., Perkin Trans. 1, 2002, 1083 DOI: 10.1039/B200415A

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Journal of the Chemical Society, Perkin Transactions 1

Approaches to the synthesis of (2R,3S)-2-hydroxymethylpyrrolidin-3-ol (CYB-3) and its C(3) epimer: a cautionary tale

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Approaches to the synthesis of (2R,3S)-2-hydroxymethylpyrrolidin-3-ol (CYB-3) and its C(3) epimer: a cautionary tale

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