Highly stereoselective and efficient total synthesis of (+)-laurencin.
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.
Baek
Seungyoup
S
College of Pharmacy, Seoul National University, San 56-1, Shillim-Dong, Kwanak-Ku, Seoul 151-742, Korea.
Jo
Hyunil
H
Kim
Hansoo
H
Kim
Hyoungsu
H
Kim
Sanghee
S
Kim
Deukjoon
D
D000478:Alkylation; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D035964:Oxocins / Q000138:chemical synthesis*; D013237:Stereoisomerism
D004988:Ethers, Cyclic; D035964:Oxocins; C017460:laurencin