| DC 欄位 |
值 |
語言 |
| DC.contributor | 化學學系 | zh_TW |
| DC.creator | 劉信緯 | zh_TW |
| DC.creator | Shin-wei Liu | en_US |
| dc.date.accessioned | 2010-7-21T07:39:07Z | |
| dc.date.available | 2010-7-21T07:39:07Z | |
| dc.date.issued | 2010 | |
| dc.identifier.uri | http://ir.lib.ncu.edu.tw:444/thesis/view_etd.asp?URN=972203020 | |
| dc.contributor.department | 化學學系 | zh_TW |
| DC.description | 國立中央大學 | zh_TW |
| DC.description | National Central University | en_US |
| dc.description.abstract | 本篇論文研究分為兩個部分：
(1) 利用掌性的雙烯雙醇((3R,4R)-hexa-1,5-diene-3,4-diol)48為起始物
合成(-)-Pachastrissamin((-)-5)與
(-)-4-epi-(-)-Pachastrissamine(8)。由於本實驗室過去利用雙烯雙醇48合成許多天然物，因此可將之視為重要的中間物。在此我們利用保護後之48先進行Sharpless環氧化反應，並將另一羥基做上保護。之後進行交叉置換(cross metathesis)反應、氫化，然後進行合環反應，最後建構出胺基，合成出(-)-4-epi-(-)-Pachastrissamine。未來我們希望將四氫呋喃環51之C4上的立體位向反轉，進而合成出(-)-Pachastrissamine。
(2) 利用掌性的雙烯雙醇((3R,4R)-hexa-1,5-diene-3,4-diol)48為起始物合成(-)-Lentiginosine。合成出吲哚啶77後，隨即將77之酮基去除，最後再將保護基除去，就可以合成出(-)-Lentiginosine((-)-66)。
| zh_TW |
| dc.description.abstract | There are two topics in this thesis:
(1) (-)-4-epi-(-)-Pachastrissamine (8) was synthesized using (3R,4R)-hexa-1,5-diene-3,4-diol (48) as the starting material. The synthesis of pachastrissamines applied some key transformations including Sharpless epoxidation of the protected diene-diol, cross metathesis (CM) with 1-tetradecene, hydrogenation, cyclization andinstallation of the amino group. (-)-Pachastrissamin((-)-5) could be prepared after the inversion of the stereocenter at C4.
(2) (-)-Lentiginosine ((-)-66) was also synthesized from (3R,4R)-hexa-1,5-diene-3,4-diol. My contribution to this work was to reduce the ketone functional group of
(1R, 2R, 8aR)-2-(tert-butyldimethylsilyloxy)-1-(methoxymethoxy)hexa
hydroindolizin-7-one (77). After screening several reducingmethods, I found that the sequence of the 1,3-dithiolane formationand Rany-Ni reduction was the most efficient.
| en_US |
| DC.subject | 分子內SN2合環反應 | zh_TW |
| DC.subject | ( - ) -Le n t i g i n o s i n e | en_US |
| DC.subject | (-)-Pachastrissamin | en_US |
| DC.subject | ( - ) -4-epi - ( - ) -Pachas t r is samine | en_US |
| DC.title | (-)-Pachastrissamine與其4-epimer的合成 | zh_TW |
| dc.language.iso | zh-TW | zh-TW |
| DC.title | Total synthesis of (-)-Pachastrissamine and it's 4-epimer | en_US |
| DC.type | 博碩士論文 | zh_TW |
| DC.type | thesis | en_US |
| DC.publisher | National Central University | en_US |