Synthetic studies toward (+)-CJ-12,950 for the stereochemical elucidation and structure activity relationship studies

2016 Fiscal Year Final Research Report

• Project/Area Number: 26460003
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: University of Toyama
• Principal Investigator: Sugimoto Kenji 富山大学, 大学院医学薬学研究部(薬学), 准教授 (60400264)
• Project Period (FY): 2014-04-01 – 2017-03-31
• Keywords: CJ-12,950 / 不斉全合成 / 閉環メタセシス / 大環状ラクトン

Outline of Final Research Achievements

Based on the convergent synthetic strategy for CJ-12,950, we realized the total synthesis of a possible diastereomer of CJ-12,950. Sharpless asymmetric epoxidation and Keck asymmetric allylation were utilized for the construction of the key chiral centers on the macrolactone. Furthermore, we found that the Zhan-1b catalyst works much better than the Grubbs or Hoveyda-Grubbs catalyst for the ring closing metathesis and [Cp*RhCl2]2-mediated coupling reaction of O-pivaloyl hydroxamic acid with pinacol vinylboronate was critical for the pendant amide formation.

Free Research Field

有機合成化学