Studies on the Total synthesis of passifloricin A

Abstract

Polyketide natural products exhibit a tremendous variety of biological activities and chemical structures, making them attractive starting points for the synthesis of natural product based libraries. Particularly, chiral polyketide units are important fragments of many natural products, especially macrolide antibiotics, ionophores and the immunosuppressant. Ten years ago the polyketide-type α-pyrone passifloricin A was isolated from the resin of Passiflora foetida var. hispida. The compound has been found to display interesting anitiprotozoal properties. Our purpose of this research is to synthesize Passifloricin A as briefly as possible without chiral induction reagent. Our starting material is chiral epoxide e.g. (S)-epichlorohydrin and (R)-glycidol. This chiral epoxide is the source of chiral hydroxyl group. Our key reaction is shown below. [원문참조]

There are the two routes to the Passifloricin A with using above two key reactions. The first route is using Sharpless Asymmetric dihydroxylation, the second route is using 3-bromobenzylmagnesium bromide. This thesis will discuss the reactions about both routes to the Passifloricin A.