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Synlett 1991; 1991(12): 857-858
DOI: 10.1055/s-1991-20901
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A New Cyclization of Olefinic Epoxides by Modified Organoaluminum Reagents via Epoxide Rearrangement and Subsequent Intramolecular Ene Reaction

Keiji Maruoka* , Noriaki Murase, Takashi Ooi, Hisashi Yamamoto
  • *Department of Applied Chemistry, Nagoya University, Chikusa, Nagoya 464-01, Japan
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Publication Date:
07 March 2002 (online)

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A new, general synthetic method for 6-membered carbocycles has been demonstrated which involves the stereocontrolled cyclization of γ,δ-unsaturated epoxides with methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) (MABR) via epoxide rearrangement and subsequent intramolecular ene reaction. This strategy is quite useful in the stereoselective synthesis of the basic skeleton of various terpenes.