title: Highly stereoselective and efficient total synthesis of (+)-laurencin.
abstract: A highly stereoselective and efficient asymmetric total synthesis of (+)-laurencin (1) has been accomplished from the known oxazolidinone 5 in 15 steps. The route features an efficient internal alkylation to form oxocene 3 from 4 and a novel use of acetonitrile anion as a two-carbon acetaldehyde equivalent for direct synthesis of ketone 2 from alpha-alkoxy amide 3.
authors.affiliation: College of Pharmacy, Seoul National University, San 56-1, Shillim-Dong, Kwanak-Ku, Seoul 151-742, Korea.
authors.forename: Seungyoup
authors.initials: S
authors.lastname: Baek
authors.forename: Hyunil
authors.initials: H
authors.lastname: Jo
authors.forename: Hansoo
authors.initials: H
authors.lastname: Kim
authors.forename: Hyoungsu
authors.initials: H
authors.lastname: Kim
authors.forename: Sanghee
authors.initials: S
authors.lastname: Kim
authors.forename: Deukjoon
authors.initials: D
authors.lastname: Kim
mesh_terms: D000478:Alkylation; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D035964:Oxocins / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D004988:Ethers, Cyclic; D035964:Oxocins; C017460:laurencin