Superacid‐Catalyzed Cyclization of Methyl (6Z)‐Geranylfarnesoates |
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| Authors: | Marina Grinco Veaceslav Kulciţki Nicon Ungur Wieslaw Jankowski Tadeusz Chojnacki Pavel F. Vlad |
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| Affiliation: | 1. Institutul de Chimie al Academiei de ?tiin?e a Moldovei, str. Academiei, 3, MD 2028, Chi?in?u, Republic of Moldova (phone/fax: +373‐22‐739‐775);2. Institute of Biochemistry and Biophysics, Polish Academy of Sciences, A. Pawi?skiego 5a, 02‐106 Warszawa, Poland |
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| 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. |
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| Keywords: | Terpenoids Cyclization reactions Super acids Scalaranes Cheilanthanes (6Z)‐Geranylfarnesoates, methyl |
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