Oxidative Degradations of the Side Chain of Unsaturated Ent-labdanes. Part II 英文参考文献.docVIP

Molecules 2007, 12, 2605-2620 molecules ISSN 1420-3049 ? 2007 by MDPI /molecules Full Paper Oxidative Degradations of the Side Chain of Unsaturated Ent-labdanes. Part II Luis Espinoza Catalán 1,*, Karen Catalán Marín 1, Héctor Carrasco Altamirano 2, Mauricio Cuellar Fritis 3 and María Cristina Chamy 2 1 Departamento de Química, Universidad Técnica Federico Santa María, Av. Espa?a N° 1680, Valparaíso, Chile 2 Departamento de Ciencias Químicas, Universidad Andrés Bello, Campus Vi?a del Mar, Los Fresnos N° 52, Vi?a del Mar, Chile 3 Facultad de Farmacia, Universidad de Valparaíso, Av. Gran Breta?a N° 1093, Valparaíso, Chile * Author to whom correspondence should be addressed; E-mail: luis.espinozac@usm.cl. For part I, see reference 19. Received: 30 October 2007; in revised form: 17 December 2007 / 21 December 2007 Abstract: A route for the degradation of the side chain of ent-labdane derivatives has been devised, 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 shall be 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 ring opening in alkaline or acid media gave rise in all cases to the formation of tricyclic compounds. Keywords: Ent-labdanes, selective degradations, unsaturated side chain. Introduction Diterpenoids with labdanic structures are a very important natural source of hydrocarbon skeletons which have been used in the elaboration of a great number of drimane compounds with remarkable biological properties, among which their olfactory [1-3], antifeedant [4], antimicrobial, cytotoxic [5], growth regulator [6], herbicidal and insecticidal activities [7-10] may be mentioned.  Molecules 2007, 12 2606 An important group of chemical reactions are those involving degradations of the side