Chemistry
A simple synthesis of 6-hydroxynorleucine based on the rearrangement of an N-nitrosodichloroacetamide
Document Type
Article
Abstract
6-Hydroxynorleucine is a versatile chemical intermediate that has found broad use in target-oriented syntheses of numerous biologically active molecules. Despite its widespread use, and despite the various strategies that have been reported for its preparation, however, this compound remains an expensive building block, which suggests that the development of new and efficient synthetic strategies for its preparation could substantially impact a wide field of biochemical research. Herein we report a strategy to synthesize 6-hydroxynorleucine from l-lysine in a one-purification sequence that replaces the side chain's nitrogen atom with an oxygen by rearranging an N-nitrosodichloroacetamide group into the corresponding ester.
Publication Title
Tetrahedron Letters
Publication Date
1-27-2016
Volume
57
Issue
4
First Page
502
Last Page
504
ISSN
0040-4039
DOI
10.1016/j.tetlet.2015.12.070
Keywords
Hydroxynorleucine, Lysine, Nitrosoamide, Rearrangement
Repository Citation
McCarthy, Blaine G.; Macarthur, Nicholas S.; and Jakobsche, Charles E., "A simple synthesis of 6-hydroxynorleucine based on the rearrangement of an N-nitrosodichloroacetamide" (2016). Chemistry. 118.
https://commons.clarku.edu/chemistry/118
Cross Post Location
Student Publications
