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Superacid-Catalyzed Cyclization of Methyl (6Z)-Geranylfarnesoates

✍ Scribed by Marina Grinco; Veaceslav Kulciţki; Nicon Ungur; Wieslaw Jankowski; Tadeusz Chojnacki; Pavel F. Vlad

Publisher
John Wiley and Sons
Year
2007
Tongue
German
Weight
84 KB
Volume
90
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

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 CC bond in these and other biologically relevant substrates plays an essential role in the cyclization process.

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