Isocomene

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Isocomene
Isocomene.svg
Isocomene-3D-balls.png
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
PubChem CID
UNII
  • InChI=1S/C15H24/c1-11-6-9-14(4)12(2)10-13(3)7-5-8-15(11,13)14/h10-11H,5-9H2,1-4H3/t11-,13+,14+,15-/m1/s1 X mark.svgN
    Key: SAOJPWFHRMUCFN-UQOMUDLDSA-N X mark.svgN
  • InChI=1/C15H24/c1-11-6-9-14(4)12(2)10-13(3)7-5-8-15(11,13)14/h10-11H,5-9H2,1-4H3/t11-,13+,14+,15-/m1/s1
    Key: SAOJPWFHRMUCFN-UQOMUDLDBQ
  • CC1=C[C@]3(C)CCC[C@@]32[C@H](C)CC[C@@]12C
  • C[C@@H]1CC[C@@]2([C@]13CCC[C@]3(C=C2C)C)C
Properties
C15H24
Molar mass 204.357 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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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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