Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Formal Synthesis of Isocomene

  • Hyo Won Lee (Department of Chemistry, Chungbuk National University) ;
  • Jae Hyun Lee (Korea Research Institute of Chemical Technology) ;
  • Ihl-Young Choi Lee (Korea Research Institute of Chemical Technology)
  • Published : 1991.08.20
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Abstract

A stereocontrolled synthesis of (${\pm}$)-isocomene (1) via selective monoketalization of tricyclo[6.3.0.$0^{1.5}$]undeca-4,7-dione(13) was reported. Grignard reaction of bicyclic enone 10, which was prepared from 2-methyl-1,3-cyclopentadione, gave the 1,4-addition product 11. The subsequent aldol condensation product 12 was converted to mesyl derivative 13. Transformation from 13 to the desired product 19 was achieved by a series of reactions, i.e., the selective monoketalization at C-4 carbonyl group, the elimination of a mesyl group, Birch alkylation, methylation at C-6, the reduction of carbonyl group, the dehydration of alcohol 18, and hydrolysis of the ketal group.

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References

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  1. ChemInform Abstract: Formal Synthesis of Isocomene. vol.23, pp.8, 1991, https://doi.org/10.1002/chin.199208279
  2. Toward the Racemic Total Synthesis of Hederacines A and B: Construction of an Advanced Tricyclic Intermediate vol.13, pp.9, 1991, https://doi.org/10.1021/ol2004353