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- Title
Superacid-Catalyzed Cyclization of Methyl (6Z)-Geranylfarnesoates.
- Authors
Marina Grinco; Veaceslav Kulciţki; Nicon Ungur; Wieslaw Jankowski; Tadeusz Chojnacki; Pavel 4;F. Vlad
- Abstract
Methyl (2Z,6Z,10E,14E)- (3) and methyl (2E,6Z,10E,14E)-geranylfarnesoate (4) were prepared, and then individually cyclized in the presence of the superacid FSO3H. 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, (6Z)-configured C=C bond in these and other biologically relevant substrates plays an essential role in the cyclization process.
- Subjects
SUPERACIDS; RING formation (Chemistry); STEREOISOMERS; CHEMICAL reactions
- Publication
Helvetica Chimica Acta, 2007, Vol 90, Issue 6, p1223
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.200790122