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

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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Abstract

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 3.0).
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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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