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Experimente zum kompetitiven Einbau der Stereoisomeren des Farnesols in Cantharidin. 6. Mitteilung zur Biosynthese des Cantharidins
Author(s) -
Woggon WolfDietrich,
Peter Martin G.,
Schmid Hans
Publication year - 1977
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19770600719
Subject(s) - farnesol , cantharidin , chemistry , stereochemistry , biochemistry , organic chemistry
Experiments on the competitive incorporation of farnesol‐stereoisomers into cantharidin Farnesol ( 2 ) has been demonstrated to be an efficient precursor for cantharidin ( 1 ), into which it is transformed by elimination of C(1), C(5), C(6), C(7) and C(7′) [1]. The following incorporation experiments with doubly labelled ( 3 H and 14 C) stereoisomers of farnesol present strong evidence that ( E , E )‐ farnesol (( E , E )‐ 2 ) in fact is the precursor for cantharidin, whereas (2 E , 6 Z )‐ 2 and ( Z , Z )‐ 2 are not utilized for the biosynthesis of cantharidin. A possible mechanism for the incorporation of (2 Z ,6 E )‐farnesol ((2 Z ,6 E )‐ 2 ) to an extent of 56,8% relative to ( E , E )‐ 2 is discussed.