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Isocomene


Isocomene is a sesquiterpene first isolated from the perennial herb southern goldenbush (Isocoma wrightii), from which it derives its name. Its unusual structure consisting of three fused cyclopentane rings was first described by Zalkow et al. in 1977. The key steps are a photocatalyzed intramolecular [2 + 2] cycloaddition reaction followed by a rearrangement reaction which forms three contiguous chiral centers.

References

References

  1. (1977). "Isocomene: A novel sesquiterpene from Isocoma Wrightii. X-Ray crystal structure of the corresponding diol". Journal of the Chemical Society, Chemical Communications.
  2. Michael C. Pirrung. (1979). "Total synthesis of (±)-isocomene". Journal of the American Chemical Society.
  3. Nicolaou, K. C.. (1996). "Classics in Total Synthesis". VCH.
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