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

[Display omitted] Described herein is a versatile approach to (i) (2 S,3 S,4 S)-3-hydroxy-4-methylproline 3, a constituent of echinocandins and related oligopeptide antibiotics; (ii) (2 S,3 S)-3-hydroxyproline 1; (iii) (2 R,3 S)-3-hydroxyprolinol 5, and (iv) 4′- tert-butoxyamido-2′-deoxythymidine 6b...

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Published inTetrahedron: asymmetry Vol. 15; no. 24; pp. 3899 - 3910
Main Authors Meng, Wei-Hua, Wu, Tian-Jun, Zhang, Hong-Kui, Huang, Pei-Qiang
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 13.12.2004
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
GEISSMAN-WAISS LACTONE
N-ACYLIMINIUM IONS
ENANTIOSELECTIVE SYNTHESIS
DIASTEREOSELECTIVE SYNTHESIS
ECHINOCANDIN-LIKE LIPOPEPTIDE
ALPHA-AMINO-ACIDS
STEREOSELECTIVE-SYNTHESIS
REGIOSELECTIVE REDUCTION
TRANSITION-STATE ANALOG
CYCLOPEPTIDE ALKALOIDS
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Summary:[Display omitted] Described herein is a versatile approach to (i) (2 S,3 S,4 S)-3-hydroxy-4-methylproline 3, a constituent of echinocandins and related oligopeptide antibiotics; (ii) (2 S,3 S)-3-hydroxyproline 1; (iii) (2 R,3 S)-3-hydroxyprolinol 5, and (iv) 4′- tert-butoxyamido-2′-deoxythymidine 6b. The method features a stepwise regio- and diastereoselective reductive furylation of the protected (3 S,4 S)-4-methylmalimide 10, ( S)-malimide 9, and a chemoselective oxidative transformation of the furyl group to the carboxyl group as the key steps.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2004.10.030