本篇論文是以D-ribose作為起始物合成目標天然物(+)-Pericosine A-C。主要的反應有Wittig 反應、Swern 氧化。以[-(Alkoxycarbonyl)-vinyl]aluminum 作具有非鏡像選擇性的羰基加成反應得到中間產物8a和 8b。雖然此非鏡像混合物可以管柱層析法分離，我們也發展出改變反應條件 ( 添加過氯酸鋰 ) 可以得到不同的主產物，並探討了此非鏡像立體選擇性的原因。化合物8a經由甲基化反應( methylation )、環合置換 ( Ring-Closing Metathesis ) 反應合環，可得到天然物 (+)-Pericosine B。化合物8b使用相同的策略可以合成天然物 (+)-Pericosine C。而天然物(+)-Pericosine A可在8a經由環合置換反應後，參考Stevenson教授的合成方法而得。

Successfully synthesizing natural product (+)-Pericosine A-C was the aim. The main reactions are Wittig reaction and Swern oxidation. Diastereomeric intermediates 8a and 8b were acquired through [-(Alkoxycarbonyl)-vinyl]aluminum doing stereoselective nucleophilic reaction. Though diastereomers 8a and 8b could be separated by column chromatography, changing reaction condition by adding LiClO4 was found to result in different major product; simultaneously, we did some researches on the cause leading to different stereoselectivity. Natural product (+)-Pericosine B was synthesized by compound 8a subjected to methylation, Ring-Closing Metathesis. On the other hand, natural product (+)-Pericosine C was obtained by using the same way as (+)-Pericosine B on compound 8b. Last but not least, (+)-Pericosine A was obtained by using compound 8a through Ring-Closing Metathesis directly referring to Prof. Stevenson’s method.

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