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
CAS Number	71629-00-0 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	24600167 ;
PubChem CID	188113;
UNII	UF2Y987D5F ;
CompTox Dashboard (EPA)	DTXSID50992204 ;
	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	204.357 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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

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