A mild and efficient synthesis of monofluorinated α-lactam pseudopeptides via a novel dehydrofluorination of Ugi products

Nianjin Liu; Song Cao; Jingjing Wu; Li Shen; Jinlong Yu; Jian Zhang; Hui Li; Xuhong Qian

doi:10.1007/s11030-009-9209-x

A mild and efficient synthesis of monofluorinated α-lactam pseudopeptides via a novel dehydrofluorination of Ugi products

Mol Divers. 2010 Aug;14(3):501-6. doi: 10.1007/s11030-009-9209-x. Epub 2009 Nov 17.

Authors

Nianjin Liu¹, Song Cao, Jingjing Wu, Li Shen, Jinlong Yu, Jian Zhang, Hui Li, Xuhong Qian

Affiliation

¹ Shanghai Key Laboratory of Chemical Biology, Center of Fluorine Chemical Technology, School of Pharmacy, East China University of Science and Technology, 200237, Shanghai, China.

PMID: 19921454
DOI: 10.1007/s11030-009-9209-x

Abstract

Six novel monofluorinated α-lactam pseudopeptide derivatives were synthesized via Ugi reaction using gem-difluoromethylene-containing isocyanide as a key component, followed by dehydrofluorination of Ugi products in one pot without additional base.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Chemistry, Organic / methods*
Halogenation*
Lactams / chemical synthesis*
Lactams / chemistry
Magnetic Resonance Spectroscopy
Models, Chemical*
Peptides / chemical synthesis*
Peptides / chemistry
Solvents / chemistry

Substances

Lactams
Peptides
Solvents