# Isocomene

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

## References

1. 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](https://doi.org/10.1039/C39770000456)***

1. Michael C. Pirrung (1979). "Total synthesis of (±)-isocomene". *Journal of the American Chemical Society*. **101** (23): 7130–7131. [doi:10.1021/ja00517a087](https://doi.org/10.1021/ja00517a087)

1. Nicolaou, K. C. & E. J. Sorensen (1996). [*Classics in Total Synthesis*](https://archive.org/details/classicstotalmet00kcni). Weinheim, Germany: VCH. p. [221](https://archive.org/details/classicstotalmet00kcni/page/n246). ISBN 3-527-29284-5.

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