Natural Product Synthesis by Utilizing Small Ring Hydrocarbons Possessing Hetero Substituents

2017 Fiscal Year Final Research Report

• Project/Area Number: 15H03806
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Hokkaido University
• Principal Investigator: Tanino Keiji 北海道大学, 理学研究院, 教授 (40217146)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Keywords: 小員環 / 開環反応 / 環化反応 / 酸素求核剤

Outline of Final Research Achievements

New synthetic reactions utilizing small ring hydrocarbons with hetero substituents were developed. A bicyclo[4.2.0]octane derivative was synthesized on the basis of the intramolecular cyclization reaction of a vinyl sulfide possessing a leaving group. A new divinylcyclobutane rearrangement reaction was developed by using 2,2-divinylcyclobutanecarbonitrile as a useful building block. The adduct derived from the four-membered nitrile and a cyclohexanone derivative was treated with an acid, giving rise to a bicyclo[6.4.0]undecane derivative via the Cope rearrangement.
On the other hand, squarate dianion was found to exhibit high reactivity as an oxygen nucleophile, which enabled the transformation of primary and secondary chlorides and bromides to the corresponding alcohols in high yields.

Free Research Field

有機合成化学