Isocomene

Isocomene

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 (Jmol)	Interactive image Interactive image
ChemSpider	24600167
PubChem	188113
InChI 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 Key: SAOJPWFHRMUCFN-UQOMUDLDSA-N 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
SMILES 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
Chemical formula	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 naturally occurring sesquiterpene first isolated from the rayless golden rod 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 first total synthesis of isocomene was published by M.C. Pirrung in 1979.^[1] The key steps are a photocatalyzed intramolecular [2 + 2] cycloaddition reaction followed by a rearrangement reaction which forms three contiguous chiral centers.^[2]

References

1. Michael C. Pirrung (1979). "Total synthesis of (±)-isocomene". Journal of the American Chemical Society. 101 (23): 7130–7131. doi:10.1021/ja00517a087.
2. Nicolaou, K. C.; E. J. Sorensen (1996). Classics in Total Synthesis. Weinheim, Germany: VCH. p. 221. ISBN 3-527-29284-5.