2006年5月
Stereoselective synthesis of 3,6-disubstituted-3,6-dihydropyridin-2-ones as potential diketopiperazine mimetics using organocopper-mediated anti-S(N)2 ' reactions and their use in the preparation of low-molecule CXCR4 antagonists
JOURNAL OF ORGANIC CHEMISTRY
- 巻
- 71
- 号
- 10
- 開始ページ
- 3942
- 終了ページ
- 3951
- 記述言語
- 英語
- 掲載種別
- DOI
- 10.1021/jo060390t
- 出版者・発行元
- AMER CHEMICAL SOC
Organocopper-mediated anti-S(N)2 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-S(N)2' 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.
- リンク情報
-
- DOI
- https://doi.org/10.1021/jo060390t
- J-GLOBAL
- https://jglobal.jst.go.jp/detail?JGLOBAL_ID=200902217957674578
- PubMed
- https://www.ncbi.nlm.nih.gov/pubmed/16674071
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000237417400036&DestApp=WOS_CPL
- ID情報
-
- DOI : 10.1021/jo060390t
- ISSN : 0022-3263
- J-Global ID : 200902217957674578
- PubMed ID : 16674071
- Web of Science ID : WOS:000237417400036