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An Effective and Highly Stereoselective Julia Olefination of Cyclopropyl Carbinol Mediated by CeCl3·7H2O/NaI
journal contribution
posted on 2005-07-07, 00:00 authored by Wei-Dong Z. Li, Yu PengAn 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.
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isomer 12diterpene 17acyclic terpenoidsstereoselective synthesisrefluxing acetonitrileolefinationiterative incorporationCeClplaunotol 6 Emethylcyclopropyl ketoneLewis acidic systemditerpene diolfunctionalized trisubstituted EC 5 prenylation synthonCyclopropyl Carbinol MediatedStereoselective Julia Olefinationcyclopropyl carbinol derivatives
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