(-)-Lentiginosine was synthesized via diastereoselective aza-Michael addition.

• Main Authors: He-chu Syu, 許鶴礎
• Other Authors: Duen-ren Hou
• Format: Others
• Language: zh-TW
• Published: 2009
• Online Access: http://ndltd.ncl.edu.tw/handle/67896785371732908266

碩士 === 國立中央大學 === 化學研究所 === 97 === There are two topic in this thesis: (1) (-)-Lentiginosine (1) was synthesized using diene 52 as the strating material. The first cross metatheses (CM) reaction of protected 52 with acrolein 80 and the following protection, addition with vinylmagnesium bromide, and oxidation provided the dienone 66. The diastereoselective double aza-Michael addition of dienone 66 and benzylamine gave the piperidine compound 82. We expect that indolizidine 88 can be prepared by hydrogenation / cyclization. (-)-Lentiginosine (1) should be synthesized after deprotection. (2) The reduction reaction of derivatives of the aromatic carbamate and lithium aluminium hydride provided the hemiaminal. The relative reactivities of esters and carbamates were discussed.