Development of highly efficient synthetic processes and their applications to natural products

2014 Fiscal Year Final Research Report

• Project/Area Number: 23390003
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Chiba University
• Principal Investigator: HAMADA Yasumasa 千葉大学, 薬学研究科(研究院), 教授 (90117846)
• Project Period (FY): 2011-04-01 – 2015-03-31
• Keywords: Friedel-Crafts反応 / intramolecular reaction / palladium / [4.5]cyclohexadienone / dihydrophenanthrene / [5.5]cyclohexadienone / acid catalyst / fused hetero compound

Outline of Final Research Achievements

An intramolecular ipso-Friedel-Crafts alkylation of phenols with an allyl carbonate side chain using a transition-metal catalyst is described. Phenols with an allyl carbonate side chain gave bicycle[4.5]spirocyclohexadienones. Phenols with a biphenyl structure stereoselectively afforded 9,10-dihydrophenanthrenes. This process was successfully applied to the asymmetric synthesis of cedrelin and pararycolin, 9,10-dihydrophenanthrene natural products. Phenols with a propargyl carbonate side chain provided bicycle[5.5]spirocyclohexadienones via a bicycle[5.4]spirohexadienone intermediate. The acid-catalyzed version of the intramolecular ipso-Friedel-Crafts alkylation of phenols and indoles was also examined, which provided the fused polycyclic hetero compounds.

Free Research Field

化学系薬学