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

Autor:	Tian-Jun Wu, Wei-Hua Meng, Hong-Kui Zhang, Pei-Qiang Huang
Rok vydání:	2004
Předmět:	Inorganic Chemistry Oligopeptide Chemistry Stereochemistry Transition state analog Organic Chemistry Enantioselective synthesis Geissman-Waiss lactone 3-hydroxy-4-methylproline Physical and Theoretical Chemistry Echinocandins Catalysis
Zdroj:	Tetrahedron: Asymmetry. 15:3899-3910
ISSN:	0957-4166
DOI:	10.1016/j.tetasy.2004.10.030
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e03020d68c507b4cdc671fd4e0c7f984 https://doi.org/10.1016/j.tetasy.2004.10.030 Zobrazit plný text záznamu Full Text from ScienceDirect