Diversity-oriented asymmetric synthesis of hapalosin: construction of three small C9/C4/C3-modified hapalosin analogue libraries.
A flexible approach to the beta-hydroxy gamma-amino acid residue (fragment C) of hapalosin has been developed on the basis of the the regio- and diastereoselective Grignard reaction. The method allows the introduction of different side chains at the C9 of hapalosin. Asymmetric syntheses of hapalosin (1a), 9-homohapalosin (1b), 9-i-butyl-hapalosin (1c), 8-epi-hapalosin (epi-1a), and three small libraries diversified at C9 (3-member, 1L3), C9/ C4 (9-member, 1L9), or C9/C4/C3 (27-member, 1L27) have been produced using this method.
Dai
Chao-Feng
CF
Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, PR China.
Cheng
Fang
F
Xu
Hai-Chao
HC
Ruan
Yuan-Ping
YP
Huang
Pei-Qiang
PQ
D002851:Chromatography, High Pressure Liquid / Q000379:methods; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D019151:Peptide Library; D012680:Sensitivity and Specificity; D013237:Stereoisomerism
D047630:Depsipeptides; D007769:Lactams; D007783:Lactones; D019151:Peptide Library; C111358:hapalosin