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Synlett 1994; 1994(8): 643-645
DOI: 10.1055/s-1994-22958
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A n + 1 Strategy for Macrocyclization Based on Free-Radical Carbonylation

Ilhyong Ryu* , Kiyoto Nagahara, Hiroshi Yamazaki, Shinji Tsunoi, Noboru Sonoda
  • *Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565, Japan
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Publication Date:
18 September 2002 (online)

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The synthesis of 10-17 membered 4-oxolactones 2 from alkyl iodides 1 having an acryloxy moiety at the termini, carbon monoxide, and TTMSS (or tin hydride) takes place cleanly in moderate to good yield under free radical conditions. Low concentrations of 1 (0.005-0.01 M) are favorable for both intermolecular trap of CO and intramolecular acyl radical addition to the C-C double bond.

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