(-)-Pachastrissamine與其4-epimer的合成; Total synthesis of (-)-Pachastrissamine and it's 4-epimer

Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/43720

Title:	(-)-Pachastrissamine與其4-epimer的合成;Total synthesis of (-)-Pachastrissamine and it's 4-epimer
Authors:	劉信緯;Shin-wei Liu
Contributors:	化學研究所
Keywords:	分子內SN2合環反應;( - ) -Le n t i g i n o s i n e;(-)-Pachastrissamin;( - ) -4-epi - ( - ) -Pachas t r is samine
Date:	2010-07-21
Issue Date:	2010-12-08 14:17:07 (UTC+8)
Publisher:	國立中央大學
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)。 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.
Appears in Collections:	[Graduate Institute of Chemistry] Electronic Thesis & Dissertation

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