2006 Fiscal Year Final Research Report Summary
SYNTHETIC STUDIES OF NATURAL PRODUCTS TO ELUCIDATE BIOLOGICAL ACTIVITIES AND DEVELOP NEWLY FUNCTIONAL COMPOUNDS
| Project/Area Number |
17580092
|
|---|
| 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 |
|---|
Principal Investigator |
KIYOTA Hiromasa TOHOKU UNIVERSITY, GRADUATE SCHOOL OF AGRICULTURAL SCIENCE, ASSOCIATE PROFESSOR, 大学院農学研究科, 助教授 (30234397)
|
|---|
| Project Period (FY) |
2005 – 2006
|
| Keywords | polynactin / pamamycin / gizzerosine / pyricuol / spirofungin / pteroenone / enacyloxin / methyl jasmonate |
|---|
| Research Abstract |
・Total synthesis of macrotetrolide a and β was achieved. β showed immnosuppressive nor cytotoxic activity. Biotransformation of the biosynthetic intemediate analog of a was examined. Synthesis of northern and southern hemispheres of pamamycin 597, and southern hemisphere of 635A was achieved.
・13'S,14'R,15'S-Absolute configuration of enacyloxin IVa was elucidated using 2D NMR such as J- resolved HMBC and NOESY methods. Synthesis of the cyclohexane moiety was achieved.
・Reassignment of the stereochemistry of spiroacetal cores of spirofungin A and B was done. Formal synthesis of spirofungin was achieve.
・Absolute configuration of pyricuol was elucidated by the synthesis of unnatural enantiomer. Presumed biosynthetic intermediated of dechloromonilidiol was synthesized
・Total synthesis of tabtoxinine-β-lactam was achieved.
・Synthesis of all four diastereomers of pteroenone was achieved.
・Absolute configuration of methyl 4,5-didehydrojasmonate was determined by the synthesis of both enantiomers. Odor of the natural enantiomer was superior to the unnatural one. Probe derivative of tuberonic acid was prepared.
・Total synthesis of gizzerosine was achieved.
|
