課程大綱

課程資訊

課程名稱	藥物立體化學 Stereochemistry in Drug Research
開課學期	109-1
授課對象	醫學院藥學研究所
授課教師	梁碧惠
課號	PHARM7012
課程識別碼	423 M1320
班次
學分	2.0
全/半年	半年
必/選修	必修
上課時間	星期五3,4(10:20~12:10)
上課地點	水森415
備註	與余兆武合授總人數上限：15人
Ceiba 課程網頁	http://ceiba.ntu.edu.tw/1091PHARM7012_
課程簡介影片
核心能力關聯	核心能力與課程規劃關聯圖
課程大綱
為確保您我的權利,請尊重智慧財產權及不得非法影印
課程概述	Stereochemistry for Drug Research I Conformation and Reactivity in Diastereoisomers a. Relative Stability and Reactivity b. Ionic Elimination c. Intramolecular Rearrangement d. Neighboring Group Participation e. Molecular Elimination II Stereochemistry in Aliphatic Nucleophilic Substitution a. Conformation and Reactivity b. Neighboring Group Effects c. Allylic Halides d. Internal Return e. Epoxide Ring-Opening f. M-P-V Reduction III Conformational Analysis in Cyclohexanes a. Substituted Cyclohexanes b. Bicyclic and Tricyclic Systems c. Conformation and Reactivity IV Asymmetric Organocatalysis a. Steroid Synthesis b. Aldol Reactions c. Michael Reactions d. Mannich Reactions e. Amination of carbonyl Groups f. Halogenation of carbonyl Groups g. Aminoxylation of carbonyl Groups h. Carbohydrate Synthesis
課程目標	本課程涵蓋下列目標之瞭解 1.基本的立體化學之結構解析理論 2.不對稱合成 3. 藥物立體合成的策略
課程要求	準時上課，認真聽講與筆記。王老師—40% take home exam (請準時交）梁老師—60%
預期每週課後學習時數
Office Hours
指定閱讀	請養成習慣閱讀以下兩個期刊 Journal of the American Chemical Society Angewandte Chemie Int. Ed.
參考書目	1. Ernesr L. Eliel and Samuel H. Wilen, "Stereochemistry of Organic Compounds." John Wiley &Son: New York, 1994. 2. Peter I. Dalko, "Enantioselective Organocatalysis " Wiley-VCH Verlag GmbH&Co KGaA: Weiheim, 2007. 3. Vicent Gotor, Ignacio alfonso, Eduardo Garcia-Urdiales, Ed. “Aymmetric Organic Synthesis with Enzymes.” Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2008. 4. Christ Wolf, “Dynamic Stereochemistry of Chiral Compounds” the Royal Society of Chemistry: Cambridge, 2008. 5. Journal of the American Chemical Society 6. Angewandte Chemie Int. Ed. 7. Jie Jack Li and E. J. Corey Asymmetric Synthesis, In “Comprehensive Name Reactions, Name Reactions for Functional Group Transformations” John Wiley & Sons, Inc., NJ, USA, 2010, Chapter 1, p.1-83.
評量方式 (僅供參考)

課程進度

週次	日期	單元主題
第1週	9/18	Conformation and reactivity in diastereoisomers a. Relative stability and reactivity b. Ionic elimination c. Intramolecular rearrangement d. Neighboring group participation e. Molecular elimination
第2週	9/25	Conformation and reactivity in diastereoisomers a. Relative stability and reactivity b. Ionic elimination c. Intramolecular rearrangement d. Neighboring group participation e. Molecular elimination
第3週	10/02	Conformation and reactivity in diastereoisomers a. Relative stability and reactivity b. Ionic elimination c. Intramolecular rearrangement d. Neighboring group participation e. Molecular elimination
第4週	10/09	放假
第5週	10/16	Conformation-stability and Reactivity I
第6週	10/23	Conformation-stability and Reactivity II
第7週	10/30	1. Stereochemistry in aliphatic nucleophilic substitution a. Conformation and Reactivity b. Neighboring group effects c. Allylic halides d. Internal return
第8週	11/06	2. Stereochemistry in aliphatic nucleophilic substitution e. Epoxide ring-opening f. M-P-V reduction Conformation-stability and Reactivity II
第9週	11/13	梁碧惠 Enzymes for organic synthesis Organic catalysis-
第10週	11/20	梁碧惠 Enzymes for organic synthesis Chiral Switch
第11週	11/27	梁碧惠 Organic catalysis- Proline assisted asymmetric synthesis
第12週	12/04	梁碧惠 Assymetric synthesis -proline catalyzed
第13週	12/11	余兆武 Organometallic catalysis I
第14週	12/18	余兆武 Organometallic catalysis II and process
第15週	12/25	CASE Discussion I
第16週	1/01	OFF
第17週	1/08	Case Discussion II
第18週	01/15	期末考試梁老師的部分70％（涵蓋王老師教的部分和第二次報告的papers範圍）余老師（30％，含第一次報告的papers範圍）