Resumo

COLMAN DE SAIZARBITORIA, T.; TILLETT, S.  e  MALAUGHLIN, J.L.. DETERMINATION ON THE ABSOLUTE CONFIGURATION OF XYLOPIACIN BY MOSHR ESTER METHODOLOGY AND MOLECULAR MODELING STUDIES. Bol. Soc. Chil. Quím. [online]. 2000, vol.45, n.4, pp.521-526. ISSN 0366-1644.  http://dx.doi.org/10.4067/S0366-16442000000400002.

Xylopiacin 1, a cytotoxic mono-tetrahydrofuran Annonaceous acetogenin, hsa been isolated from the seeds of Xylopia aromatica (Lam.) Mart. (Annonaceae).  The absolute configuration of this compound was determined by its Mosher ester derivatives. The sterogenic carbinol centers of xylopiacin S-MTPA 2 and xylopiacin R-MTPA 3 have been determined by ¹H-NMR and 2D-NMR experiments utilizing Mosher esters. The preferred conformation of xylopiacin 1 and its derivatives 2 and 3 sere determined using molecular mechanics and molecular dynamics calculations

Palavras-chave : Acetogenins; absolute configuration; Mosher ester; molecular modeling.