| Project/Area Number |
11660101
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Single-year Grants |
|---|
| Section | 一般 |
|---|
| Research Field |
Bioproduction chemistry/Bioorganic chemistry
|
|---|
| Research Institution | Tohoku University (2000)
Ibaraki University (1999) |
|---|
Principal Investigator |
KUWAHARA Shigefumi Division of Life Science, Graduate School of Agricultural Science, Tohoku University, Associate Professor, 大学院・農学研究科, 助教授 (30170145)
|
|---|
| Project Period (FY) |
1999 – 2000
|
| Project Status |
Completed (Fiscal Year 2000)
|
| Budget Amount *help |
¥2,900,000 (Direct Cost: ¥2,900,000)
Fiscal Year 2000: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 1999: ¥1,800,000 (Direct Cost: ¥1,800,000)
|
|---|
| Keywords | stink bug / sesquiterpene / pheromone / cockroach / periplanone / spodoptera exigua / volicitin / leaf miner moth / Tynacantha marginata / sesquiterpene / Diels-Alder reaction / periplanone-D / periplanone-C / volicitin / 5,9-dimethylpentadecane / Perileucoptera coffeella / Spodoptera exigua / Periplaneta fuliginosa / Pheromone / Elicitor |
|---|
| Research Abstract |
Synthesis of both the racemate and optically active forms of a novel sesquiterpene (9-isopropyl-4, 6-dimethyltricyclo [4.4.0.0^<5, 9>] dec-3-en-2-one) isolated from the pheromone gland of a Brazilian predatory stink bug, Tynacantha marginata Dallas, was achieved via a intramolecular double Michael cycloaddition and intramolecular Diels-Alder reaction, respectively. This synthetic work enabled us to determine the absolute configuration of the putative pheromone in addition to the confirmation of the proposed structure. Other semiochemicals such as the sex pheromones of Periplaneta fuliginosa and Perileucoptera coffeella, and an elicitor (named volicitin) contained in the regurgitant of Spodoptera exigua were also synthesized in optically active forms. The synthesis of the sex pheromone of Periplaneta fuliginosa led to the correction of prviously reported physical and spectroscopic data of this pheromone called periplanone-D.
|
