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Synthesis and Absolute Configurations of Six Natural Phenylpropanoids
Author(s) -
Liu XueLian,
Chen HuiJun,
Yang YangYang,
Wu Yikang,
You Jun
Publication year - 2014
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.201402096
Subject(s) - absolute (philosophy) , stereocenter , chemistry , absolute configuration , optical rotation , stereochemistry , natural (archaeology) , computational chemistry , organic chemistry , enantioselective synthesis , philosophy , epistemology , archaeology , history , catalysis
In an effort to find answers to the tantalizing questions about the absolute configurations of a group of long‐known natural phenylpropanoids with very similar structures but different signs for the optical rotations, the compounds in question were synthesized in enantiomerically pure form using Evans asymmetric alkylation to generate the stereogenic centres with predefined absolute configurations. The 1 H and 13 C NMR spectra of the synthetic products were very consistent with those reported for their natural counterparts. In most cases, the optical rotations were also consistent with the corresponding data for the natural samples. The new findings not only allowed unequivocal assignments of the absolute configurations for the natural products, but also revealed that the configurations of closely related compounds from the same plant may be different.