2015 Fiscal Year Final Research Report
A new synthetic method of bioactive terpene indole alkaloids
| Project/Area Number |
24380063
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (B)
|
| Allocation Type | Partial Multi-year Fund |
|---|
| Section | 一般 |
|---|
| Research Field |
Bioproduction chemistry/Bioorganic chemistry
|
|---|
| Research Institution | Nagoya University |
|---|
Principal Investigator |
|
|---|
| Co-Investigator(Kenkyū-buntansha) |
Nakazaki Atsuo 名古屋大学, 大学院生命農学研究科, 准教授 (00366428)
|
|---|
| Project Period (FY) |
2012-04-01 – 2016-03-31
|
| Keywords | インドールアルカロイド / 有機合成 / 天然物合成 / 連続環化反応 / セスペンドール / 構造決定 |
|---|
| Outline of Final Research Achievements |
This research has focused on development of an efficient synthetic route of sespendole, a naturally occurring indole alkaloid including complex terpene structure. We plan that segment 1 including the aromatic moiety and segment 2 of the terpene moiety are separately synthesized, and then coupled together followed by cyclization of the B and C rings at the same time. Two possible diastereomers of the segment 1 were synthesized and then transformed to indole compounds. Comparison of NMR spectra of those indoles and sespendole determined relative stereochemistry of the epoxyalcohol to be syn. Investigation of coupling between two segments and tandem cyclization revealed that the former coupling was realized under a condition of the Sonogashira coupling and the latter tandem cyclization was effectively catalyzed with a Cu or Pd catalyst.
|
| Free Research Field |
天然物化学
|
