天然物(+)-Pericosine A, (-)-Pericosine C, (+)-Pericosine E的合成研究

Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/69349

Title:	天然物(+)-Pericosine A, (-)-Pericosine C, (+)-Pericosine E的合成研究
Authors:	鍾政宇;Chung,Cheng-Yu
Contributors:	化學學系
Keywords:	非鏡像選擇性;鈀催化;[α-(Alkoxycarbonyl)vinyl]aluminium reaction;allylic substitution
Date:	2016-01-08
Issue Date:	2016-03-17 18:38:54 (UTC+8)
Publisher:	國立中央大學
Abstract:	本篇研究是以D-Ribose作為起始物合成目標天然物(+)-Pericosine A, (-)-Pericosine C和(+)-Pericosine E。主要的反應有Wittig反應和Swern氧化反應。以[α-(Alkoxycarbonyl)vinyl]aluminium作為具有非鏡像選擇性的羰基加成反應可得到重要的中間產物8a和8b。(+)-Pericosine A可在化合物8a進行環合置換(Ring-Closing Metathesis)反應後，參考Stevenson教授的合成方法而得。化合物8a經由環合置換反應合環、鈀催化的allylic substitution後可得到(-)-Pericosine C。(+)-Pericosine E應亦可藉由鈀催化的allylic substitution而得，然而尚在進行中。;Successfully synthesizing natural product (+)-Pericosine A, (-)-Periciosine C,(+)-Pericosine E was the aim. The main reactions we used are Wittig reaction, Swern oxidation, [α-(Alkoxycarbonyl)-vinyl]aluminum reaction and Palladium-catalyzed allylic substitution. Diastereomeric intermediate 8a and 8b can be synthesized via [α-(Alkoxycarbonyl)-vinyl]aluminum reaction which the ratio is 4 to 1. (+)-Pericosine A was obtained by compound 8a through Ring-Closing metathesis then directly referring to Prof. Stevenson’s method. (-)-Pericosine C was obtained by compound 8a via Ring-Closing Metathesis and Palladium-catalyzed allylic substitution successfully. (+)-Pericosine E might can be synthesized by Palladium-catalyzed allylic substitution, but still doing effort right now.
Appears in Collections:	[Graduate Institute of Chemistry] Electronic Thesis & Dissertation

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