Synthesis of Biologically Active Bislactone Utilizing an Indium-mediated Reformatsky-Claisen Rearrangement and Development of Chiral Claisen Rearrangement

2014 Fiscal Year Final Research Report

• Project/Area Number: 24590011
• 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), 准教授 (80250413)
• Project Period (FY): 2012-04-01 – 2015-03-31
• Keywords: 有機合成 / 天然物合成 / 転位反応

Outline of Final Research Achievements

The asymmetric synthesis of (-)-dihydrosporothriolide, a biologically active bis-γ-butyrolactone, was achieved. The synthesis includes a D-proline-catalyzed asymmetric aminooxylation, indium-mediated Reformatsky-Claisen rearrangement of an α,α-dibromoacetate derivative, and diastereoselective dihydroxylation. The route requires no protective group manipulation and allows the concise seven-step synthesis of (-)-dihydrosporothriolide from n-octanal. The synthesis illustrates the synthetic utility of our indium-mediated Reformatsky-Claisen rearrangement applicable to base-sensitive substrates.

Free Research Field

有機合成化学