Concise Synthesis and Skeletal Diversification of Natural Products and their Variants Employing a Multipotent Intermediate.

2017 Fiscal Year Final Research Report

• Project/Area Number: 15H03117
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Chemical biology
• Research Institution: Tokyo University of Agriculture and Technology
• Principal Investigator: OGURI HIROKI 東京農工大学, 工学(系)研究科(研究院), 教授 (80311546)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Keywords: アルカロイド / 骨格多様化合成 / 多能性中間体 / ジヒドロピリジン / 生合成摸倣合成

Outline of Final Research Achievements

Exploiting a carbonyl group installed at the C3 position of the 1,6-dihydropyridine (DHP) system, we devised a strategy for cyanomethylation at C2/C6 and subsequent divergent installation of an allyl group at C3/C5 in a highly regio- and stereo-controlled manner. Installation of the gem-dimethyl groups at C6 positions could inhibit disproportionation and allowed region-controlled dimerization gaining a concise access to a halicyclamine-type skeleton.
Intramolecular hydroarylations of N-propargylated tetrahydrocarbolines were efficiently mediated by Zn(OTf)2. We systematically implemented divergent annulations involving two kinds of ring-expansion reactions and spirocyclizations that efficiently generated three distinct alkaloidal scaffolds. Furthermore, we found intriguing solvent effects of t-BuOH.

Free Research Field

有機合成化学