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Concise synthesis of 22-hydroxyacuminatine, cytotoxic camptothecinoid from Camptotheca acuminata, by pyridone

Matej Babjak1, Alice Kanazawa, Regan J Anderson

  • 1Université Joseph Fourier de Grenoble, Chimie Recherche (LEDSS), 38041, Grenoble, France.

Organic & Biomolecular Chemistry
|February 1, 2006
PubMed

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...