2013 Fiscal Year Final Research Report
Studies on the chemical synthesis of antitumor saponins for the evaluation of their biological activities
| Project/Area Number |
23590014
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Multi-year Fund |
|---|
| Section | 一般 |
|---|
| Research Field |
Chemical pharmacy
|
|---|
| Research Institution | Nagoya City University |
|---|
Principal Investigator |
SEIICHI NAKAMURA 名古屋市立大学, 薬学研究科(研究院), 教授 (90261320)
|
|---|
| Project Period (FY) |
2011 – 2013
|
| Keywords | シラシロシド類 / 抗腫瘍性サポニン / Ireland－Claisen転位 / 二連続第四級不斉中心 / ニトリルオキシド / 1,3-双極付加環化 / シクロプロパン化 / 酸化型ジテルペノイド |
|---|
| Research Abstract |
Toward the total synthesis of antitumor saponins scillascillosides, the stereoselective construction of CDE ring system of these molecules have been explored. Ireland-Claisen rearrangement of the dihydrofurancarboxylate, obtained by intramolecular O-H insertion followed by olefination, proceeded stereoselectively to give the desired stereoisomer in good yield. The product was successfully converted to the CDE ring fragment through an intramolecular 1,3-dipolar cycloaddition and introduction of an angular methyl group. With regard to the key Ireland-Claisen rearrangement, we found that the substitution pattern of the adjacent carbon atom played a pivotal role in directing the stereochemical course of the reaction, and this finding led to the development of methods for the stereodivergent syntheses of two chiral building blocks.
|
