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Total Synthesis of Plakortone B
Author(s) -
Xie XinGang,
Wu XunWei,
Lee HingKen,
Peng XiaoShui,
Wong Henry N. C.
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000189
Subject(s) - stereocenter , absolute configuration , stereochemistry , bicyclic molecule , chemistry , molecule , enantioselective synthesis , organic chemistry , catalysis
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 (3 S ,4 S ,6 R ,10 R ).