Asymmetric synthesis of passifloricin A: a correction in structure |
| |
Authors: | Juan MurgaMiguel Carda JAlberto Marco |
| |
Institution: | a Depart. de Q. Inorgánica y Orgánica, Univ. Jaume I, Castellón, E-12080 Castellón, Spain b Depart. de Q. Orgánica, Univ. de Valencia, E-46100 Burjassot, Valencia, Spain |
| |
Abstract: | The structure reported in the literature for the pharmacologically active, natural lactone passifloricin A (δ-lactone of 2Z,5R*S*,7R*,9S*,11S*-tetrahydroxyhexacos-2-enoic acid) is incorrect not only as regards stereochemical issues, but also in the placement of one of the hydroxyl groups of the side chain. By means of an unambiguous synthesis, passifloricin A is shown to be the δ-lactone of 2Z,5R,7S,9S,12S-tetrahydroxyhexacos-2-enoic acid. All of the stereogenic centres were created with the aid of Brown's asymmetric allylation methodology. The lactone ring was made via ring-closing metathesis. |
| |
Keywords: | passifloricin A lactones ring-closing metathesis asymmetric allylboration |
本文献已被 ScienceDirect 等数据库收录! |
|