Total synthesis of plakortone B.
Plakortone B is a naturally occurring bicyclic[3.3.0]furanolactone compound with attractive bioactivities. Although the relative configuration of plakortone B's central core had been established by NMR spectroscopic methods, the absolute configuration of its four stereocenters remained unknown. In the present paper, all four possible isomers of plakortone B were synthesized and one of these molecules was found to be identical with the natural plakortone B on the basis of (1)H, (13)C NMR spectra and specific rotation comparisons. Thus, the absolute configuration of the natural plakortone B was determined to be (3S,4S,6R,10R).
Xie
Xin-Gang
XG
Department of Chemistry, Centre of Novel Functional Molecules, Institute of Chinese Medicine and Institute of Molecular Technology for Drug Discovery and Synthesis, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, China.
Wu
Xun-Wei
XW
Lee
Hing-Ken
HK
Peng
Xiao-Shui
XS
Wong
Henry N C
HN
D002384:Catalysis; D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D015394:Molecular Structure; D013237:Stereoisomerism
D007783:Lactones; C517066:plakortone B