TOTAL SYNTHESIS OF THE CYTOTOXIC MACROLIDE FORMAMICIN

本课题的研究目标是合成一种新型的细胞毒性抗真菌抗生素--福霉素。作为抗生素乙内酸家族的一员，福霉素对几种白血病细胞系表现出非常强的体外细胞毒性（1C 50 = 0.13- 0.15 ng/mL）。 甲酸霉素的结构对有机化学家提出了几个合成挑战。所提出的合成是高度收敛的，并展示了一种新开发的方法，用于形成2，6-双脱氧-β-糖苷。此外，我们希望提出一种新的除了手性γ-烷氧基丙二烯基锡烷醛形成不同的保护反-1，2-炔丙基二醇在一个单一的步骤。

The goal of the proposed research plan is the develop a synthesis of formamicin, a novel cytotoxic antifungal antiobiotic. A member of the hygrolide family of antibiotics, formamicin exhibits very potent in vitro cytotoxicities towards several leukemia cell lines (1C50 = 0.13- 0.15 ng/mL). The structure of formamicin presents several synthetic challenges to the organic chemist. The proposed synthesis is highly convergent and showcases a newly developed method for the formation of 2,6-dideoxy-beta-glycosides. In addition, we wish to propose a novel addition of chiral gamma-alkoxyallenyl stannanes to aldehydes to form differently protected anti-1,2-propargylic diols in a single step.