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Diversity-oriented asymmetric synthesis of hapalosin: construction of three small C9/C4/C3-modified hapalosin

Chao-Feng Dai1, Fang Cheng, Hai-Chao Xu

  • 1Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, PR China.

Journal of Combinatorial Chemistry
|March 16, 2007
PubMed

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The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.