Synthetic study of the antitumor tricyclic diterpenoides

2016 Fiscal Year Final Research Report

• Project/Area Number: 26460016
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Tokyo University of Pharmacy and Life Science
• Principal Investigator: ABE Hideki 東京薬科大学, 生命科学部, 准教授 (00328551)
• Project Period (FY): 2014-04-01 – 2017-03-31
• Keywords: curcusone / Weinreb アミド化 / ７員環構築 / Dowd-Beckwith環拡大反応 / 向山 aldol 反応 / ケタール化 / afritoxinone A / catunaregin

Outline of Final Research Achievements

Synthetic study of tricyclic diterpenoid curcusones possess antitumor activity were demonstrated. For the reason that the polycyclic acetal compound was obtained instead of the desired product at the synthetic study of key intermediate lactone, the ring expansion reaction was performed as a new synthetic pathway to construct a seven-membered ring. Furthermore, the construction of the tricyclic skeleton of target natural compound curcusones was accomplished with several procedures including Mukaiyama aldol reaction.
On the other hand, construction of polyoxygenated framework of afritoxinone A and efficient asymmetric total synthesis of catunaregin were achieved based on the side reaction at the synthetic study of lactone moiety.

Free Research Field

有機合成化学