Application of the Diastereoselective Ketal Formation Reactions for the Organic Synthesis.

2017 Fiscal Year Final Research Report

• Project/Area Number: 15K07872
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Musashino University
• Principal Investigator: HIROYA Kou 武蔵野大学, 薬学研究所, 教授 (70192721)
• Research Collaborator: Takahashi Erina ; Nakamura Ayumi ; Fukuda Chiaki ; Hayakawa Emi ; Watanabe Akiho ; Ohkubo Mami
• Project Period (FY): 2015-04-01 – 2018-03-31
• Keywords: ジアステレオ選択的反応 / ケタール化反応 / 不斉第四級炭素 / 不斉四置換炭素 / 不斉合成 / 生物活性 / アルカロイド / 不斉ジヒドロキシル化反応

Outline of Final Research Achievements

The expansion of the substrates for the diastereoselective ketal formation reaction have been established as my primary object. The products of the diastereoselective ketal formation seem to be useful for synthetic organic chemistry. Therefore, I have arranged the synthesis of the important compounds as an optically active form for my second object.
Firstly, compounds having an aromatic ring and cinnamyl unit at C2 position of 1,3-cyclohexanedione have been synthesized and highly diastereoselective hemiketal and intermolecular ketal formation reaction have been achieved. Next, the asymmetric dihydroxylation reaction was examined utilizing commercially available reagents. As a result, the products which have almost 90%e.e. were afforded. Secondly, the conversion of the quaternary carbon center to chiral four substituted center was investigated and single lactam was obtained by Beckmann rearrangement. Synthetic studies of two natural products as optically active forms are now under way.

Free Research Field

有機化学