Premium
Synthesis and Configuration of the Phenolic Nonadecanediol Isolated from the Resinous Exudates of Heliotropium sinuatum
Author(s) -
Chen ChaoYuan,
Zhang ShaoMin,
Wu Yikang,
Gao Po
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201184
Subject(s) - enantiopure drug , chemistry , absolute configuration , diol , natural product , epoxide , stereochemistry , optical rotation , atropisomer , chirality (physics) , organic chemistry , enantioselective synthesis , chiral symmetry , catalysis , nambu–jona lasinio model , physics , quantum mechanics , quark
Abstract The (3 S ,5 R ) and (3 R ,5 R ) isomers of the title compound were synthesized from enantiopure epoxide chiral building blocks readily accessible from D ‐gluconolactone. The former (a syn ‐1,3‐diol) gave 1 H and 13 C NMR spectroscopic data and optical rotation in good agreement with those reported for the natural product, whereas distinct differences were found with the data for the latter (an anti ‐1,3‐diol). These results unambiguously showed that the absolute configuration of the natural product must be (3 S ,5 R ).