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Chemie und Stereochemie der Iridoide, XIII. Synthese von enantiomerenreinem (1 R ,2 S ,2″ Z )‐(+)‐Methyljasmonat aus Catalpol
Author(s) -
Weinges Klaus,
Lernhardt Ulrich
Publication year - 1990
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.1990199001141
Subject(s) - catalpol , chemistry , methyl jasmonate , stereochemistry , organic chemistry , glycoside , biochemistry , gene
Chemistry and Stereochemistry of Iridoids, XIII. — Synthesis of Enantiomerically Pure Methyl (1 R ,2 S ,2″ Z )‐(+)‐Jasmonate Starting from Catalpol Enantiomerically pure methyl (1 R ,2 S ,2″ Z )‐(+)‐jasmonate ( 2 ), which was recognized as a component of the fragrance of the jasmine flower oil, was synthesized starting from catalpol ( 3 ). 2 is easily epimerized to 1 . Thus, it is necessary to use very mild conditions in the course of the synthesis and purification. These results raise the question whether 2 exists as a natural product in the flower of jasmine and 1 arises during the isolation.