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Synthesis and Absolute Configuration of the Diynediol from Psathyrella scobinacea
Author(s) -
WU Jianzhong,
WU Yikang,
JIAN Yajun,
ZHANG Yihua
Publication year - 2009
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200990005
Subject(s) - chemistry , absolute configuration , absolute (philosophy) , chirality (physics) , optical rotation , specific rotation , stereochemistry , natural product , organic chemistry , philosophy , chiral symmetry breaking , physics , epistemology , quantum mechanics , nambu–jona lasinio model , quark
All the four isomers of Scobidiynediol (hepta‐4,6‐diyne‐2,3‐diol), a natural product isolated from white‐rot fungus Psathyrella scobinacea , were synthesized using either ( R )‐ or ( S )‐lactate as the source of chirality. The relative configurations of the diols were established by NOE experiments performed on the cyclic acetonides. The relative as well as absolute configurations of the natural Scobidiynediol was assigned as (2 S ,3 S ) through comparison of the optical rotation and 1 H NMR data.