Studies toward total synthesis of nigricanosides, anti-mitotic agents from a marine green alga, aiming at the elucidation of the pharmacophore
Project/Area Number |
15K01794
|
Research Category |
Grant-in-Aid for Scientific Research (C)
|
Allocation Type | Multi-year Fund |
Section | 一般 |
Research Field |
Biomolecular chemistry
|
Research Institution | Akita University |
Principal Investigator |
|
Research Collaborator |
TSUNODA Takayuki
|
Project Period (FY) |
2015-04-01 – 2018-03-31
|
Project Status |
Completed (Fiscal Year 2017)
|
Budget Amount *help |
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2017: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
|
Keywords | 全合成研究 / クライゼン転位 / 鎖状エーテル / 有糸分裂阻害剤 / 1,4-ジアルコキシ-2-ブテン / ヘンリー反応 / ラジカル脱離反応 / 立体選択的合成 / ニトロアルドール反応 |
Outline of Final Research Achievements |
Nigricanoseides, isolated from the green alga Avrainvillea nigricans, belong to a monogalactosyldiacylglycerol family and were reported to exhibit potent growth inhibition against cancer cells due to their anti-mitotic activity. Based on the absolute stereochemistry of nigricanoside A dimethyl ester elucidated by Ready and coworkers in 2015, a new convergent total synthesis of the compound was planned to realize the efficient supply. So far, the ether-cross-linkages between the upper and the lower fatty acid chains and between the lower fatty acid chain and the galactose moiety have been constructed based on chirality transferring Ireland-Claisen rearrangement. A prototype synthetic route to the right-half segment of nigricanoside A dimethyl ester has also been developed. Furthermore, a construction method for the C9'-C10' double bond has been developed by use of model compounds having ether bonds adjacent to the reaction centers.
|
Report
(4 results)
Research Products
(6 results)
-
-
-
[Journal Article] Synthesis of the ABCDEF-ring of ciguatoxin 3C2017
Author(s)
Takuto Sato, Kenshu Fujiwara, Keisuke Nogoshi, Akiyoshi Goto, Daisuke Domon, Natsumi Kawamura, Yoshitaka Nomura, Daisuke Sato, Hideki Tanaka, Akio Murai, Yoshihiko Kondo, Uichi Akiba, Ryo Katoono, Hidetoshi Kawai, Takanori Suzuki
-
Journal Title
Tetrahedron
Volume: 73
Issue: 6
Pages: 703-726
DOI
Related Report
Peer Reviewed / Open Access
-
-
-