Synthesis of highly functionalized homochiral azetidines and azetidine-2-carboxylic esters

✍ Scribed by Annie Duréault; Martine Portal; François Carreaux; Jean Claude Depezay

• Book ID: 104203482
• Publisher: Elsevier Science
• Year: 1993
• Tongue: French
• Weight: 703 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)85738-0

✦ Synopsis

Abstracf : Homo&ml (2s. 3S)-3-bewyloxy-2-formykeMioes 2, (2s. 3Sj-3-buq40xy-2eahmeho xy-dk 3 and the highly sfminexl (2s)-N-pmetboxypheuyl-2-silyloxymetbyl-3-az&dinone 4 were. successfully synt&eaix.ed starting from diethyl-L-tartrate. The suitably fonctionali azetidine ring is formed in a single synthetic operation with minimum Protecting group chemistry. Functionalized azetidine-2carboxylic acids such as 2-carboxy-3-hydroxy-azetidine, the azetidine moiety of 3-hydroxy mugineic acid, a typical phytosiderophorel, or such as polyoximic acid: (2s,E)-3ethylidene-azetidine2+zboxylic acid2, a constituent of hipeptidyl polyoxins (nucleoside antibiotics with fungicidal properties) am met in the nature. ,,Jqmo%oo~ OH il 3-hydroxy mugineic acid LOCONH, . ---.I Po&oxin K, R=H Nat& polyhydroxylated azetidines are also encountered although they are not as widespread as are the pyrrolidines derivatives. Recently two sphingosinedetived azetidine alkaloids, possessing potent actomyosin AT&-activating activity were isolated from marine sponge and their structure was elucidated3.