Preparation of Seven-Membered Cyclic Ethers Containing Halogenated Side Chains by Acetal-Alkene Cyclizations

Daniel Berger; Larry E. Overman

doi:10.1055/s-1992-21501

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Synlett 1992; 1992(10): 811-813
DOI: 10.1055/s-1992-21501

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Preparation of Seven-Membered Cyclic Ethers Containing Halogenated Side Chains by Acetal-Alkene Cyclizations

Daniel Berger^* , Larry E. Overman

^*Department of Chemistry, University of California, Irvine, CA 92717, USA

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Publication Date:
08 March 2002 (online)

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Lewis acid-promoted cyclizations of β-chloro- (or β-bromo-) acetals prepared from vinyl ethers, 4-(trimethylsilyl)-4-penten-1-ols and Cl₂ (or Br₂) afford 2,3,6,7-tetrahydrooxepins containing 1-chloroalkyl (or 1-bromoalkyl) side chains at carbon 2. The chloride-containing cis-2,7-disubstituted-Δ⁴-oxepene ring system of the marine lipid isolaurepinnacin can be efficiently assembled in this way.