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Superacid‐Catalyzed Cyclization of Methyl (6 Z )‐Geranylfarnesoates
Author(s) -
Grinco Marina,
Kulciţki Veaceslav,
Ungur Nicon,
Jankowski Wieslaw,
Chojnacki Tadeusz,
Vlad Pavel F.
Publication year - 2007
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.200790122
Subject(s) - superacid , chemistry , catalysis , substrate (aquarium) , selectivity , stereochemistry , medicinal chemistry , organic chemistry , oceanography , geology
Methyl (2 Z ,6 Z ,10 E ,14 E )‐ ( 3 ) and methyl (2 E ,6 Z ,10 E ,14 E )‐geranylfarnesoate ( 4 ) were prepared, and then individually cyclized in the presence of the superacid FSO 3 H. In the case of substrate 3 , the scalaranic ester 9 (26%) and the cheilanthanic ester 10 (39%) were isolated. Under the same conditions, substrate 4 afforded a mixture of the corresponding stereoisomers 11 (25%) and 12 (63%). The observed product selectivity supports that the internal, (6 Z )‐configured CC bond in these and other biologically relevant substrates plays an essential role in the cyclization process.