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

作者: Wei-Hua Meng , Tian-Jun Wu , Hong-Kui Zhang , Pei-Qiang Huang

DOI: 10.1016/J.TETASY.2004.10.030

关键词:

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

参考文章(110)
Robert S. Gordee, Manuel Debono, Thomas R. Parr, The Fungal Cell Wall — A Target For Lipopeptide Antifungal Agents New Approaches for Antifungal Drugs. pp. 46- 63 ,(1992) , 10.1007/978-1-4899-6729-9_4
John S. Wolff, James D. Ogle, Milan A. Logan, Studies on 3-Methoxyproline and 3-Hydroxyproline Journal of Biological Chemistry. ,vol. 241, pp. 1300- 1307 ,(1966) , 10.1016/S0021-9258(18)96774-8
Liren Jin, Hong Wu, Huailing Wu, Peiqiang Huang, Kyeongeun Jung, Hong Lim, Enantioselective Synthesis of Pyrrolydinonyl Thymine Nucleoside Analogues Chemistry Letters. ,vol. 28, pp. 687- 688 ,(1999) , 10.1246/CL.1999.687
Karl-Heinz Altmann, Pyrrolidine based analogs of 3′-deoxythymidine Tetrahedron Letters. ,vol. 34, pp. 7721- 7724 ,(1993) , 10.1016/S0040-4039(00)61548-4
Bruce E. Maryanoff, Han-Cheng Zhang, Judith H. Cohen, Ignatius J. Turchi, Cynthia A. Maryanoff, Cyclizations of N-acyliminium ions. Chemical Reviews. ,vol. 104, pp. 1431- 1628 ,(2004) , 10.1021/CR0306182
Rudolf Tschesche, Samuel T. David, J. Uhlendorf, Hans-Wolfram Fehlhaber, Alkaloide aus Rhamnaceen, XV. Mucronin-D, ein weiteres cyclisches Peptid-Alkaloid aus Zizyphus mucronata Willd Chemische Berichte. ,vol. 105, pp. 3106- 3114 ,(1972) , 10.1002/CBER.19721050933
John C. Sheehan, D. Mania, Shoshiro. Nakamura, John A. Stock, Kenji. Maeda, The structure of telomycin. Journal of the American Chemical Society. ,vol. 90, pp. 462- 470 ,(1963) , 10.1021/JA01004A043
TOSHIRO IWAMOTO, AKIHIKO FUJIE, KAZUTOSHI SAKAMOTO, YASUHISA TSURUMI, NOBUHARU SHIGEMATSU, MICHIO YAMASHITA, SEIJI HASHIMOTO, MASAKUNI OKUHARA, MASANOBU KOHSAKA, WF11899A, B and C, novel antifungal lipopeptides. I. Taxonomy, fermentation, isolation and physico-chemical properties. The Journal of Antibiotics. ,vol. 47, pp. 1084- 1091 ,(1994) , 10.7164/ANTIBIOTICS.47.1084