2014 Fiscal Year Final Research Report
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 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Toho University |
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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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| 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 |
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| 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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| Free Research Field |
有機化学
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