一、Systhesis of Prostaglandin analogs二、To Explore the Synthetic Route toward Fawcettimine-type Lycopodium Alkaloids三、To Explore the Synthetic Path of Tamiflu

• Main Authors: Kai-Ming Cheng, 鄭凱銘
• Other Authors: Tu-Hsin Yan
• Format: Others
• Language: zh-TW
• Published: 2019
• Online Access: http://ndltd.ncl.edu.tw/handle/23ymxd

碩士 === 國立中興大學 === 化學系所 === 107 === 1. Prostaglandin-derived functional group synthesis Because glaucoma drugs are expensive and the synthesis steps are complicated, we try to increase the weight of the drug to reduce its demand. Therefore, we synthesized a functional group and tried to replace it. Taking diethyl malonate as a starting material, reacting with formaldehyde to form a diol, protecting with a protecting group, then removing the monoester ester group, and deprotecting by reduction and digestion. The 2-(bromomethyl)propane-1,3-diyl dinitrate glaucoma functional group product was synthesized in seven steps. 2. Study on the synthetic route of Fawcettimine-type stone pine alkaloids In the past, the Fawcettimine compounds in the laboratory were reacted with oxygen and nitrogen heteroatoms [3+2]. However, the Lewis acid TiCl4 could not be completed due to its influence of oxygen and nitrogen. Therefore, this study mainly uses halogen or double bonds. The compound is firstly converted into a olefin structure, and after the [3+2] reaction, a multi-step functional group modification is carried out to obtain a Fawcettimine compound. 3. Study on the synthetic route of Tamiflu The starting tartaric acid compound is used as a starting material. After esterification and triamyl alcohol protection, the DIBAL position is used for selective reduction, and then the Grignard reagent is used to form a diene, followed by a second-generation Grubb catalyst to form a ring. The ring opening reaction is carried out with a Lewis acid and a reducing agent, followed by modification with a multi-step functional group to obtain a product Tamiflu compound.