학술논문
Synthesis of the N-(tert-butyloxycarbonyl)-O-triisopropylsilyl-d-pyrrolosamine glycal of lomaiviticins A and B via epimerization of l-Threonine
Document Type
Journal Article
Source
Quick submit: 2017-05-11T14:35:24-0400
Morris, William J., and Matthew D. Shair. 2010. “Synthesis of the N-(tert-Butyloxycarbonyl)-O-Triisopropylsilyl-d-Pyrrolosamine Glycal of Lomaiviticins A and B via Epimerization of l-Threonine.” Tetrahedron Letters 51 (33) (August): 4310–4312. doi:10.1016/j.tetlet.2010.06.028.
Morris, William J., and Matthew D. Shair. 2010. “Synthesis of the N-(tert-Butyloxycarbonyl)-O-Triisopropylsilyl-d-Pyrrolosamine Glycal of Lomaiviticins A and B via Epimerization of l-Threonine.” Tetrahedron Letters 51 (33) (August): 4310–4312. doi:10.1016/j.tetlet.2010.06.028.
Subject
Language
English
ISSN
0040-4039
Abstract
An efficient synthesis of the N-(tert-butyloxycarbonyl)-O-triisopropylsilyl-D-pyrrolosamine glycal of lomaiviticin A (1) and lomaiviticin B (2) is described. The synthesis is highlighted by the epimerization of the L-threonine-derived oxazolidine 10 to oxazolidine 11. This key epimerization reaction, which serves to establish the correct relative configuration of the carbohydrate unit, was made possible only after conformational analysis indicated that substituted oxazolidines may adopt conformations that preclude enolization.
Chemistry and Chemical Biology
Chemistry and Chemical Biology