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Elsevier, Tetrahedron: Asymmetry, 24(15), p. 3899-3910, 2004

DOI: 10.1016/j.tetasy.2004.10.030

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Asymmetric syntheses of protected (2S,3S,4S)-3-hydroxy-4-methylproline and 4 ‘-tert-butoxyamido-2 ‘-deoxythymidine

Journal article published in 2004 by Wh Meng, 黄培强, 张洪奎, Tj Wu, Hk Zhang, Pq Huang ORCID
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

Described herein is a versatile approach to (i) (2S,3S,4S)-3-hydroxy-4-methylproline 3, a constituent of echinocandins and related oligopeptide antibiotics; (ii) (2S,3S)-3-hydroxyproline 1; (iii) (2R,3S)-3-hydroxyprolinol 5, and (iv) 4'-tert-butoxyamido-2'-deoxythymidine 6b. The method features a stepwise regio- and diastereoselective reductive furylation of the protected (3S,4S)-4-methylmalimide 10, (S)-malimide 9, and a chemoselective oxidative transformation of the furyl group to the carboxyl group as the key steps. (C) 2004 Elsevier Ltd. All rights reserved.