Stereocomplementary reactions for preparing multi-substituted olefins and its application to distinctive molecules

2017 Fiscal Year Final Research Report

• Project/Area Number: 15K05508
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Kwansei Gakuin University
• Principal Investigator: Yoo Tanabe 関西学院大学, 理工学部, 教授 (30236666)
• Co-Investigator(Renkei-kenkyūsha): MISAKI Tomonori 兵庫県立大学, 大学院理学研究科, 助教 (00411786) ; NISHII Yoshinori 信州大学, 繊維学部, 准教授 (40332259)
• Research Collaborator: NAKATSUJI Hidefumi 関西学院大学, 理工学部, 助教 (80751817) ; ASHIDA Yuichiro 関西学院大学, 大学院理工学研究科, リサーチアシスタント
• Project Period (FY): 2015-10-21 – 2018-03-31
• Keywords: 立体選択的合成 / 多置換オレフィン / プロセス化学 / 立体補完的合成 / パラレル合成 / 医薬 / トシル化 / クロスカップリング

Outline of Final Research Achievements

A divergent synthetic methodology producing E- and Z-stereodefined multi-substituted olefin scaffolds has been performed. The present protocols, which are directed for process chemistry, involve highly substrate-general E- and Z-stereocomplementary parallel syntheses. As distinctive applications, the first parallel syntheses of a couple of notable and useful pharmaceuticals were accomplished. That is (1) parallel synthesis of SSRI-drug, Zimelidine, without use of resolution method, and (2) parallel synthesis of cancer-treatment drug, Tamoxifen, a representative synthetic motif of all-carbon (fully)-substituted olefins. This methodology was highlighted in “Synform,” which is the journal introducing a notable synthetic chemistry.
During the course of study, we could propose two “Organic syntheses” procedures, which document practical methods with reproducibility for important synthetic building blocks.

Free Research Field

有機合成化学