中文摘要

本論文利用樟腦磺醯胺1,3-二環戊-4-酮掌性101，與γ-甲氧基巴豆酸甲酯行 Michael 反應，先建立兩個連續的掌性中心，再接著做 α-羥基化反應來得到三個連續的掌性中心，隨後再行內酯化反應脫去掌性輔助基得到內酯104。使用Grubbs 2nd generation Catalyst 延長碳鏈得到內酯108。期望再經由官能基轉換可得到天然物(+)-Cinatrin C3。

Abstract

This thesis dealt with the application of camphor-derived 1,3-dioxolan-4-one 101 in the synthesis of Cinatrin Family. Asymmetric Michael addition of 101 with methyl crotonate followed by α-hydroxylation with saccharin-type Davis reagent, then spontaneous lactonization gave highly functionalized lactone 104. Lactone 104 underwent olefin metathesis with 1-undecene in presence of second generation Grubbs catalyst to give lactone 108. Lactone 108 is an important precursor for the synthesis of nature product (+)-Cinatrin C3.

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