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An Effective and Highly Stereoselective Julia Olefination of Cyclopropyl Carbinol Mediated by CeCl3·7H2O/NaI

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journal contribution
posted on 07.07.2005 by Wei-Dong Z. Li, Yu Peng
An efficient and highly stereoselective synthesis of functionalized trisubstituted E-olefins from cyclopropyl carbinol derivatives via a Julia-type olefination mediated by an intriguing Lewis acidic system consisting of CeCl3·7H2O and NaI in refluxing acetonitrile is reported. This facile olefination allows for the iterative incorporation of methylcyclopropyl ketone as a C5 prenylation synthon in the synthesis of acyclic terpenoids, as demonstrated in the facile synthesis of plaunotol 6E-isomer 12, a biologically significant diterpene diol, and naturally occurring diterpene 17.