Synthetic studies on portimine, a potent and selective inducer of apoptosis

2017 Fiscal Year Final Research Report

• Project/Area Number: 15K07861
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Nagasaki University
• Principal Investigator: ISHIHARA Jun 長崎大学, 医歯薬学総合研究科(薬学系), 教授 (80250413)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Keywords: 有機合成化学 / 海産天然物 / 全合成 / 環状アセタール / ポルチミン

Outline of Final Research Achievements

In late years, apoptosis has been revealed to play an important role for cancer and autoimmune disease. Portimine is a polycyclic marine toxin isolated from the dinoflagellate. The biological studies of this compound indicated that it has potent antitumor activity and also shows the activation of caspases indicating apoptotic activity. In this work, we studied the synthesis of portimine, which contains five-membered cyclic mine moiety and remarkable dioxabicyclo[6.2.1]undecanone embedded in macrocyclic framework. Brown's asymmetric crotylation and silyl linkage-mediated coupling afforded an acyclic key intermediate. This acyclic compound was subjected to acid to generate a core acetal.

Free Research Field

有機合成化学