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Chemie und Stereochemie der Iridoide, XIX. Zwei einfache EPC‐Synthesen mit chemischem Beweis der absoluten Konfiguration von (+)‐Mitsugashiwa‐Lacton aus ( S )‐(−)‐Citronellol und Aucubin
Author(s) -
Weinges Klaus,
Ziegler Hans Jürgen,
Maurer Wolfgang,
Schmidbauer Stefan B.
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301163
Subject(s) - chemistry , citronellol , stereochemistry , chromatography , geraniol , essential oil
Chemistry and Stereochemistry of Iridoids, XIX. – Two Straightforward EPC Syntheses with Chemical Evidence of Absolute Configuration of (+)‐Mitsugashiwa Lactone from ( S )‐(−)‐Citronellol and Aucubin Enantiomerically pure (+)‐Mitsugashiwa lactone ( 9 ) was prepared in eight steps from ( S )‐(−)‐citronellol ( 1 ), whereas only four steps were required for the conversion of hexaacetylaucubin ( 10 ) into 9 . Both starting materials are readily available in large quantities. The synthesis of 9 from 1 establishes the absolute configuration at C‐7 in 9 . Conversely, the synthesis of 9 from 10 confirms the absolute configuration at C‐4a and C‐7a in 9 .