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Preparation of Kingiside from Aucubin
Author(s) -
Weinges Klaus,
Schick Hartmut,
Ziegler Hans Jürgen
Publication year - 2000
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/(sici)1099-0690(200004)2000:8<1623::aid-ejoc1623>3.0.co;2-y
Subject(s) - aucubin , loganin , chemistry , caprifoliaceae , epimer , stereochemistry , iridoid , organic chemistry , botany , high performance liquid chromatography , glycoside , biology
The tetraacetyl derivative 8 of the naturally occurring kingiside ( 8a ) was prepared from aucubin ( 1 ). Intermediates in the synthesis were (8 S )‐tetraacetyl loganin ( 6 ) and (8 S )‐tetraacetyl‐7‐ketologanin ( 7 ), whose free (8 R )‐epimers occur in many different plants (Caprifoliaceae, Loganiaceae). The 13 C NMR spectrum allows the structure to be unequivocally identified.