Synthetic study of gregatin derivateves with palladium (II) catalyst
Project/Area Number |
24790026
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Research Category |
Grant-in-Aid for Young Scientists (B)
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Allocation Type | Multi-year Fund |
Research Field |
Chemical pharmacy
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Research Institution | Toho University |
Principal Investigator |
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Co-Investigator(Renkei-kenkyūsha) |
KATO Keisuke 東邦大学, 薬学部, 教授 (80276609)
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Project Period (FY) |
2012-04-01 – 2015-03-31
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Project Status |
Completed (Fiscal Year 2014)
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Budget Amount *help |
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2014: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2013: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2012: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
|
Keywords | パラジウム / カルボニル化 / グレガチン / スルホキシド / オキサゾリン / パラジウム触媒 / フラノン |
Outline of Final Research Achievements |
The first total synthesis of (+)-gregatin E and a new total synthesis of (+)-gregatin B was carried out. Key features of our synthetic approach involve a palladium-catalyzed cyclization-methoxycarbonylation of optically active propargylic acetate and a Suzuki-Miyaura coupling or CuTC-mediated coupling reaction. The absolute configuration of (+)-gregatin E (5R, 5’S) was determined. Asymmetric cyclization-methoxycarbonylation of 1,1-diethynylacetate mediated by chiral palladium (II) complex afforded orthoesters in good yield with good enantioselectivity. Orthoesters were easily converted to franones and therefore the formal synthesis of gregatin B and E were achieved.
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Report
(4 results)
Research Products
(8 results)
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[Presentation] グレガチンBの合成研究
Author(s)
日下部太一, 河合泰子, 加藤恵介
Organizer
第65回有機合成化学協会関東支部シンポジウム
Place of Presentation
新潟薬科大学(新潟)
Related Report
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