Development and Application of Methods for Constructing New Skeletons by Use of Ring-Rearrangement Metathesis and Biomimetic Reactions

2017 Fiscal Year Final Research Report

• Project/Area Number: 15K05504
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Keio University
• Principal Investigator: Takao Ken-ichi 慶應義塾大学, 理工学部(矢上), 教授 (70287481)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Keywords: メタセシス / 骨格変換 / 天然物合成 / シクロブテンカルボン酸 / ブテノリド / 生合成模倣反応

Outline of Final Research Achievements

In the field of synthetic organic chemistry, a revolutionary new strategy is needed to achieve “the ideal synthesis”. From this perspective, we focused on sequential metathesis and developed a novel ring-rearrangement metathesis, which allows the one-pot transformation of a strained cyclobutenecarboxylate into a γ-butenolide. In this study, further applications of the ring-rearrangement metathesis were examined and a biomimetic reaction was used to construct more complex structures of natural products. As a result, we achieved the total synthesis and structural revision of clavilactone D. In addition, we succeeded in the synthesis of a biogenetic precursor of aquatolide.

Free Research Field

有機合成化学