Synthetic study on furofuran lignans by means of control of electronic properties of phenol

2015 Fiscal Year Final Research Report

• Project/Area Number: 26860013
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Chemical pharmacy
• Research Institution: University of Shizuoka
• Principal Investigator: Inai Makoto 静岡県立大学, 薬学部, 助教 (20621626)
• Project Period (FY): 2014-04-01 – 2016-03-31
• Keywords: セサミン / セサミノール / ヘジオトール A / 不斉アルドール反応 / フロフランリグナン / 有機触媒

Outline of Final Research Achievements

Furofuran lignans isolated from various vascular plants have been reported to exhibit antitumor, antioxidant, antiviral, and antihypertensive activities, as well as inhibition of low-density lipoprotein oxidation. These furofuran lignans and their derivatives are expected to be useful as lead compounds for drug development.
In this research, plant products (+)-hedyotol A, (+)-sesamin, (+)-sesaminol, (+)-methylpiperitol, (+)-aschantin, and (+)-5'-hydroxymethylpiperitol were synthesized in a highly stereocontrolled manner through proline-catalyzed cross-aldol reaction, followed by biomimetic construction of the furofuran lignan skeleton through a quinomethide intermediate.

Free Research Field

天然物合成化学