Resumo

KESTERNICH, VICTOR; CONTRERAS-ORTEGA, CARLOS  e  MARTINEZ, ROLANDO. A THEORETICAL STUDY OF THE STEREOCHEMICAL COURSE OF THE ACID CYCLIZATION OF TWO 5-OXOGERMACREN- 6,12-OLIDES EPIMERIC IN C4. Bol. Soc. Chil. Quím. [online]. 2001, vol.46, n.3, pp.271-279. ISSN 0366-1644.  http://dx.doi.org/10.4067/S0366-16442001000300006.

The theoretical study of both the conformational distribution and the acid cyclization of two epimeric 5-oxogermacren-6,12-olides in C4 is described. Our results on the stereochemistry of the cyclization products, 5-hydroxyguaian-6,12-olides, agree with experimental results reported previously. Curtin-Hammet principle and Hammond postulate are used to propose reaction pathways consistent with above results. The theoretical results were obtained by using a MM2 program from HyperChem 4.5

Palavras-chave : Sesquiterpenic lactones; germacranolides; guaianolides; MM2 program.