Synthetic Studies toward (+)-Fawcettimine

• Main Authors: Ko-Tung Wang, 王科棟
• Other Authors: Tu-Hsin Yang
• Format: Others
• Language: zh-TW
• Published: 2010
• Online Access: http://ndltd.ncl.edu.tw/handle/13743786765313335807

碩士 === 國立中興大學 === 化學系所 === 98 === (+)-Fawcettimine has a tetracyclic framework containing a single quaternary carbon center.Stereocontrolled coupling addition of methyl 3-iodopropanate-derived zinc reagent to (+)-5-methyl-2-cyclohexenone, Application of the base-promated intramolecular Dieckmann condensation and a regiocontolled C-alkylation of 1,3-diketone enolate with t-butyl N-allyl,N-(2-bromoethyl)carbamate,and then implementation of a regioselective installation of enol triflate and palladium-catalyzed intramolecular coupling between triflate with alkene moiety led efficient to a readily separable mixture of tricyclic dienic ketone and its regioisomer..Chemoselective hydrogenation of dienic ketone with H2/Pd/C in MeOH proceeded without complication to give the monounsaturated tricyclic keto carbamate,which serves as a pivotal precursor to (+)-Fawcettimine.