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Synthesis of Phenostereum A and Related Diol and Attempted Assignment of Relative Configurations of Remote Stereocenters by 13 C NMR
Author(s) -
Yu YanChao,
Liu Bo,
Wu Yikang
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600657
Subject(s) - stereocenter , enantiopure drug , diastereomer , carbon 13 nmr , diol , chemistry , stereochemistry , organic chemistry , enantioselective synthesis , catalysis
Phenostereum A 1 and the related diol 2 were synthesized in enantiopure forms. The diasteromers of different relative configurations showed delicate differences in 13 C NMR, revealing mutual influences between the remote stereocenters in such compounds for the first time. Nevertheless, the data for diastereomers of different relative configurations were all fully consistent with those for the natural ones by conventional criteria; assignment of the relative configurations by 13 C NMR thus remained impossible. Indications for the relative configurations of the natural products were found by comparison of the 13 C NMR deviations from the data for synthetic isomers. The structures for several other natural 2,3‐dihydrobenzofurans were also either confirmed or disproved by synthesis.