title: Short and versatile route to a key intermediate for lactacystin synthesis.
abstract: [reaction: see text] A key intermediate 14 for the synthesis of lactacystin 1 has been constructed in four steps and 33% overall yield. The key steps involve cyclization of a suitably functionalized glutamic acid derivative and concomitant alkylation of the resulting beta,beta-diketoester system, C-acylation of the cyclic alpha-amidoketone 9, and decarboxylbenzylation of 12. Alkylation of a related beta,beta-diketoester 5 was additionally achieved with several electrophiles.
authors.affiliation: Department of Chemistry, Loughborough University, Loughborough, Leicestershire LE11 3TU, England. pcbpage@lboro.ac.uk
authors.forename: Philip C
authors.initials: PC
authors.lastname: Bulman Page
authors.forename: A Sazali
authors.initials: AS
authors.lastname: Hamzah
authors.forename: David C
authors.initials: DC
authors.lastname: Leach
authors.forename: Steven M
authors.initials: SM
authors.lastname: Allin
authors.forename: David M
authors.initials: DM
authors.lastname: Andrews
authors.forename: Gerasimos A
authors.initials: GA
authors.lastname: Rassias
mesh_terms: D000111:Acetylcysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D000215:Acylation; D000478:Alkylation; D003500:Cyclization; D018698:Glutamic Acid / Q000737:chemistry; D015394:Molecular Structure
chemical_list: C067713:lactacystin; D018698:Glutamic Acid; D000111:Acetylcysteine