Macroexpansion methodology. Medium ring synthesis based on an eight unit ring expansion process

  • Wender P
  • Sieburth S
  • Petraitis J
 et al. 
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Treatment of 1,2-(E,E)-di(1-buta-1,3-dienyl)cyclohexanol (21) with potassium hydride in tetrahydrofuran at room temperature resulted in the facile formation of a 14-membered ring dienolate which on kinetic protonation provided cyclotetradeca-3,5,7-trien-1-one. This novel rearrangement which provides the basis for an efficient, eight unit ring expansion method was also observed when 5,8-dimethyl-5-hydroxy-1,3,7,9-decapentaene (28), the acyclic analogue of 21, was treated with potassium hydride in tetrahydrofuran. Methodology for the preparation of 21 and 28 including the preparation of 1-lithio-1,3-butadiene is also described. © 1981.

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  • Sunil SinghNRCPB new delhi

  • Paul A. Wender

  • Scott Mc N. Sieburth

  • Joseph J. Petraitis

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