Concise total synthesis of (±)-aloperine and 6-epi-aloperine

被引:19
作者
Passarella, D [1 ]
Angoli, M [1 ]
Giardini, A [1 ]
Lesma, G [1 ]
Silvani, A [1 ]
Danieli, B [1 ]
机构
[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
关键词
D O I
10.1021/ol0263144
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Total synthesis of aloperine and 6-epi-aloperine is reported. The crucial steps of the synthetic strategy are an aza-annulation reaction and an intermolecular Diels-Alder reaction. The synthetic plan proceeds from commercially available piperidine-2-ethanol.
引用
收藏
页码:2925 / 2928
页数:4
相关论文
共 52 条
[21]   On the reactivity of 1-amino-3-siloxy-1,3-dienes: Kinetics investigation and theoretical interpretation [J].
Kozmin, SA ;
Green, MT ;
Rawal, VH .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) :8045-8047
[22]   Preparation and Diels-Alder reactivity of 1-amino-3-siloxy-1,3-butadienes [J].
Kozmin, SA ;
Rawal, VH .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) :5252-5253
[23]   1-amino-3-siloxy-1,3-butadienes: Highly reactive dienes for the Diels-Alder reaction [J].
Kozmin, SA ;
Janey, JM ;
Rawal, VH .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :3039-3052
[24]   A general strategy to Aspidosperma alkaloids:: Efficient, stereocontrolled synthesis of tabersonine [J].
Kozmin, SA ;
Rawal, VH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (51) :13523-13524
[25]   Chiral amino siloxy dienes in the Diels-Alder reaction:: Applications to the asymmetric synthesis of 4-substituted and 4,5-disubstituted cyclohexenones and the total synthesis of (-)-α-elemene [J].
Kozmin, SA ;
Rawal, VH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) :9562-9573
[26]   Asymmetric Diels-Alder reactions of chiral 1-amino-3-siloxy-1,3-butadiene: Application to the enantioselective synthesis of (-)-alpha-elemene [J].
Kozmin, SA ;
Rawal, VH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (30) :7165-7166
[27]  
KUCHKAROV S, 1976, SB NAUCHN T TASHK UN, V108
[28]  
KUCHKAROV S, 1978, KHIM PRIR SOEDIN, V44
[29]  
KUCHKAROV S, 1979, KHIM PRIR SOEDIN, V413
[30]   C-13 CHEMICAL-SHIFTS OF METHYLQUINOLIZIDINES AND CORRELATIONS WITH CHEMICAL-SHIFTS OF METHYL-SUBSTITUTED TRANS-DECALINS [J].
LALONDE, RT ;
DONVITO, TN .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1974, 52 (22) :3778-3783