An operationally simple and fully regiocontrolled formal total synthesis of the montanine-type Amaryllidaceae alkaloid (±)-pancracine

被引:21
|
作者
Banwell, MG [1 ]
Edwards, AJ [1 ]
Jolliffe, KA [1 ]
Kemmler, M [1 ]
机构
[1] Australian Natl Univ, Res Sch Chem, Inst Adv Studies, Canberra, ACT 0200, Australia
关键词
D O I
10.1039/b102252k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of beta- nitrostyrene 4 with cyclohexane-1,3-dione (5) in the presence of DBU affords the Michael-addition product 6, which is readily elaborated, using straightforward chemistry, to the 5,11-methanomorphanthridine 2, acquisition of which constitutes a formal total synthesis of the racemic modification of the montanine alkaloid pancracine (1).
引用
收藏
页码:1345 / 1348
页数:4
相关论文
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  • [21] Potential intermediate, (+/-)-di-o-acetyl-3 alpha-phenylselanyl-3,3a-dihydro-B-nor-6,7a-secolycorin-5-one for synthesis of the amaryllidaceae alkaloid lycorine: Formal and total syntheses of (+/-)-lycorine
    Hoshino, O
    Ishizaki, M
    Kamei, K
    Taguchi, M
    Nagao, T
    Iwaoka, K
    Sawaki, S
    Umezawa, B
    Iitaka, Y
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (06): : 571 - 580