Practical synthesis of a 3, 4, 4a, 5, 8, 8a-hexahydro-2H-isoquinoline-1, 6-dione ring system by the diels-alder reaction of an optically active dienophile, a 5, 6-dihydro-1H-pyridin-2-one derivative, with siloxydiene

被引:0
|
作者
Nakagawa, M [1 ]
Uchida, H [1 ]
Ono, K [1 ]
Kimura, Y [1 ]
Yamabe, M [1 ]
Watanabe, T [1 ]
Tsuji, R [1 ]
Akiba, M [1 ]
Terada, Y [1 ]
Nagaki, D [1 ]
Ban, S [1 ]
Miyashita, N [1 ]
Kano, T [1 ]
Theeraladanon, C [1 ]
Hatakeyama, K [1 ]
Arisawa, M [1 ]
Nishida, A [1 ]
机构
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
关键词
D O I
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中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient method for preparing chiral 3-substituted-5, 6-dihydro-1H-pyridin-2-one (1) in large scale, based on a modification of our previous method, is described. The large scale Diels-Alder reaction of I with siloxydiene (2) to synthesize hexahydroisoquinoline-1, 6-dione, which is a key intermediate for the synthesis of manzamine alkaloids, was also studied.
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页码:721 / 733
页数:13
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