Development of a divergent synthesis of 4- and 5-membered heterocycles and its application to the synthesis of bioactive natural product

2013 Fiscal Year Final Research Report

• Project/Area Number: 24790012
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Chemical pharmacy
• Research Institution: Kinki University (2013); Osaka University (2012)
• Principal Investigator: MAEGAWA Tomohiro 近畿大学, 薬学部, 准教授 (40363890)
• Project Period (FY): 2012-04-01 – 2014-03-31
• Keywords: O,P-アセタール / オキセタン / 複素環合成 / 天然物合成 / 創薬化学

Research Abstract

Heterocyclic compounds are utilized in pharmaceuticals, agrochemicals and functional materials. Recently, oxygen-containing 4-membered heterocycles, oxetane, has been reported as a useful skeleton to improve a pharmaceutical quality. We developed a facile oxetane synthesis using O,P-acetal consisted of phosphorous and oxygen as a key intermediate. The feature of this method is eco-conscious double use of phosphorous atom in one reaction. We also succeeded in synthesizing natural product having anticancer activity in short steps using our method.

Research Products

• [Journal Article] Method for the Efficient Synthesis of Highly-Substituted Oxetan- and Azetidin?, Dihydrofuran- and Pyrrolidin-3-ones and Its Application to the Synthesis of (±)- Pseudodeflectusin (2012)
  • Author(s): 前川智弘、大竹和樹、廣澤渓一、後藤章広、藤岡弘道
  • Journal Title: Organic Letters Volume: 14 Pages: 4798-4801
  • DOI: 10.1021/ol302096j
  • Peer Reviewed
• [Presentation] Intramolecular Cyclization Using Phosphonate-stabilized Anion : Efficient Synthesis of Highly-Substituted Oxetan- and Azetidin-, Dihydrofuran- and Pyrrolidin-3-ones and Its Application (2013)
  • Author(s): 前川智弘、大竹和樹、廣澤渓一、後藤章広、藤岡弘道
  • Organizer: 10^<th> International Symposium on Carbanion Chemistry
  • Place of Presentation: 京都
  • Year and Date: 2013-09-24
• [Presentation] (2012)
  • Author(s): 前川智弘、大竹和樹、廣澤渓一、後藤章広、藤岡弘道
  • Organizer: 第6回武田科学振興財団薬科学シンポジウム
  • Place of Presentation: 大阪
  • Year and Date: 2012-09-13
• [Presentation] (2012)
  • Author(s): 前川智弘、大竹和樹、廣澤渓一、後藤章広、藤岡弘道
  • Organizer: 日本プロセス化学会2012サマーシンポジウム
  • Place of Presentation: 京都
  • Year and Date: 2012-07-20
• [Presentation] (2012)
  • Author(s): 前川智弘、大竹和樹、廣澤渓一、後藤章広、藤岡弘道
  • Organizer: 第10回次世代担う有機化学シンポジウム
  • Place of Presentation: 大阪
  • Year and Date: 2012-05-11