Isocomene

Isocomene
Ball-and-stick model of the isocomene molecule
Names
IUPAC name
(3aS,5aS,8aR)-1,3a,4,5a-Tetramethyl-1,2,3,3a,5a,6,7,8-octahydrocyclopenta[c]pentalene
Identifiers
3D model (JSmol)
ChemSpider
Properties
C15H24
Molar mass 204.36 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Isocomene is a sesquiterpene first isolated from the perennial herb southern goldenbush (Isocoma wrightii),[1] from which it derives its name. Its unusual structure consisting of three fused cyclopentane rings was first described by Zalkow et al. in 1977.[1] The first total synthesis of isocomene was published by M.C. Pirrung in 1979.[2] The key steps are a photocatalyzed intramolecular [2 + 2] cycloaddition reaction followed by a rearrangement reaction which forms three contiguous chiral centers.[3]

References

  1. 1 2 Zalkow, L. H; Harris, R. N; Van Derveer, D; Bertrand, J. A (1977). "Isocomene: A novel sesquiterpene from Isocoma Wrightii. X-Ray crystal structure of the corresponding diol". Journal of the Chemical Society, Chemical Communications (13): 456. doi:10.1039/C39770000456.
  2. ↑ Michael C. Pirrung (1979). "Total synthesis of (±)-isocomene". Journal of the American Chemical Society. 101 (23): 7130–7131. doi:10.1021/ja00517a087.
  3. ↑ Nicolaou, K. C.; E. J. Sorensen (1996). Classics in Total Synthesis. Weinheim, Germany: VCH. p. 221. ISBN 3-527-29284-5.
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