Total synthesis of (-)-Pachastrissamine and it''s 4-epimer

• Main Authors: Shin-wei Liu, 劉信緯
• Other Authors: Duen-ren Hou
• Format: Others
• Language: zh-TW
• Published: 2010
• Online Access: http://ndltd.ncl.edu.tw/handle/69361643757284330673

碩士 === 國立中央大學 === 化學研究所 === 98 === 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.