Synthesis and configuration of the cyclin-dependent kinase inhibitor roscovitine and its enantiomer

S D Wang, S J McClue, J R Ferguson, J D Hull, S Stokes, S Parsons, R Westwood, P M Fischer

Research output: Contribution to journalArticlepeer-review

Abstract

The cyclin-dependent kinase inhibitor (R)-2-(6-benzylamino-9-isopropyl-9H-purin-2-ylamino)butan-1-ol (roscovitine, 1a), as well as its (S)-enantiomer 1b, were synthesised. The chemical structure and absolute configuration of both enantiomers was confirmed by X-ray crystallography. Furthermore, high enantiomeric excess (>98%) was demonstrated by chiral chromatography of la and 1b, as well as NMR analysis of the diastereomeric Mosher's ester derivatives 2a and 2b. (C) 2001 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)2891-2894
Number of pages4
JournalTetrahedron: Asymmetry
Volume12
Issue number20
Publication statusPublished - 13 Nov 2001

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