Stereoselective synthesis of 3,6-disubstituted-3,6-dihydropyridin-2-ones as potential diketopiperazine mimetics using organocopper-mediated anti-SN2' reactions and their use in the preparation of low-molecule CXCR4 antagonists.
Publication/Presentation Date
5-12-2006
Abstract
Organocopper-mediated anti-SN2' reactions of gamma-phosphoryloxy-alpha,beta-unsaturated-delta-lactams were used to prepare highly functionalized diketopiperazine mimetics. The substrate phosphates 24, 32, and 47 were prepared from alpha-amino acid-derived allylic alcohols 10 by a sequence of reactions that included ring-closing metathesis. In the reactions of phosphates with organocopper reagents, the addition of LiCl dramatically improved anti-SN2' selectivity, indicating that an organocopper cluster containing lithium chloride plays an important role in the determination of regioselectivity. This reaction system was applied to the preparation of novel low molecular weight CXCR4-chemokine receptor antagonists.
Volume
71
Issue
10
First Page
3942
Last Page
3951
ISSN
0022-3263
Published In/Presented At
Niida, A., Tanigaki, H., Inokuchi, E., Sasaki, Y., Oishi, S., Ohno, H., Tamamura, H., Wang, Z., Peiper, S. C., Kitaura, K., Otaka, A., & Fujii, N. (2006). Stereoselective synthesis of 3,6-disubstituted-3,6-dihydropyridin-2-ones as potential diketopiperazine mimetics using organocopper-mediated anti-SN2' reactions and their use in the preparation of low-molecule CXCR4 antagonists. The Journal of organic chemistry, 71(10), 3942–3951. https://doi.org/10.1021/jo060390t
Disciplines
Business Administration, Management, and Operations | Health and Medical Administration | Management Sciences and Quantitative Methods
PubMedID
16674071
Department(s)
Administration and Leadership
Document Type
Article