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Molecules 2007, 12(12), 2605-2620; doi:10.3390/12122605

Oxidative Degradations of the Side Chain of Unsaturated Ent-labdanes. Part II

1,* , 1, 2, 3 and 2
1 Departamento de Química, Universidad Técnica Federico Santa María, Av. España N° 1680, Valparaíso, Chile 2 Departamento de Ciencias Químicas, Universidad Andrés Bello, Campus Viña del Mar, Los Fresnos N° 52, Viña del Mar, Chile 3 Facultad de Farmacia, Universidad de Valparaíso, Av. Gran Bretaña N° 1093, Valparaíso, Chile
* Author to whom correspondence should be addressed.
Received: 30 October 2007 / Accepted: 17 December 2007 / Published: 21 December 2007
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A route for the degradation of the side chain of ent-labdane derivatives has beendevised, giving the useful synthon 2β,12-dihydroxy-13,14,15,16,17-pentanor-ent-labdane-8-one (8). The use of this compound in the preparation of terpenylquinone derivatives shallbe reported elsewhere. In addition we have synthesized the compound 2β,12-diacetoxy-8β,17-epoxy-13,14,15,16-tetranor-ent-labdane (10), which upon catalytic epoxide ringopening in alkaline or acid media gave rise in all cases to the formation of tricycliccompounds.
Keywords: Ent-labdanes; selective degradations; unsaturated side chain. Ent-labdanes; selective degradations; unsaturated side chain.
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Catalán, L.E.; Marín, K.C.; Altamirano, H.C.; Fritis, M.C.; Chamy, M.C. Oxidative Degradations of the Side Chain of Unsaturated Ent-labdanes. Part II. Molecules 2007, 12, 2605-2620.

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