A biomimetic synthesis of (-)-N(a)-methylervitsine

被引:14
作者
Bennasar, ML [1 ]
Zulaica, E
Alonso, Y
Mata, I
Molins, E
Bosch, J
机构
[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain
[2] CSIC, Inst Ciencia Mat, Cerdanyola Del Valles 080193, Spain
关键词
D O I
10.1039/b102010m
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A straightforward, biomimetic synthesis of (-)-N-(a)-methylervitsine involving the nucleophilic addition of the enolate derived from 2-acetylindole 1 to chiral, non-racemic pyridinium salt 2, followed by (Me2N+=CH2) I- induced cyclization of the resultant 1,4-dihydropyridine, with subsequent elaboration of the exocyclic 16-methylene and 20E-ethylidene substituents, is reported.
引用
收藏
页码:1166 / 1167
页数:2
相关论文
共 29 条
[1]  
Amann R, 1996, LIEBIGS ANN, P349
[2]  
ANDRIANTSIFERANA M, 1977, TETRAHEDRON LETT, P2587
[3]  
[Anonymous], 1996, Adv. Nitrogen Heterocycl
[4]   STEREOSELECTIVE FORMATION OF 4-SUBSTITUTED-1,4-DIHYDRONICOTINOYL COMPLEXES UTILIZING THE CHIRAL AUXILIARY [(ETA-5-C5H5)FE(CO)(PPH3)] [J].
BECKETT, RP ;
BURGESS, VA ;
DAVIES, SG ;
WHITTAKER, M .
TETRAHEDRON LETTERS, 1993, 34 (22) :3617-3620
[5]  
Bennasar ML, 2000, EUR J ORG CHEM, V2000, P3919, DOI 10.1002/1099-0690(200012)2000:23<3919::AID-EJOC3919>3.0.CO
[6]  
2-P
[7]   Biomimetic total synthesis of ervitsine and indole alkaloids of the ervatamine group via 1,4-dihydropyridines [J].
Bennasar, ML ;
Vidal, B ;
Bosch, J .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (11) :3597-3609
[8]   Studies on the synthesis of akuammiline alkaloids.: Access to 3,4-secoakuammilan derivatives [J].
Bennasar, ML ;
Zulaica, E ;
Ramírez, A ;
Bosch, J .
TETRAHEDRON, 1999, 55 (10) :3117-3128
[9]   Nucleophilic addition of 1-acetylindole enolates to pyridinium salts.: Stereoselective formal synthesis of (±)-geissoschizine and (±)-akagerine via 1,4-dihydropyridines [J].
Bennasar, ML ;
Jiménez, JM ;
Vidal, B ;
Sufi, BA ;
Bosch, J .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (26) :9605-9612
[10]   METHOD FOR THE SYNTHESIS OF BRIDGED INDOLE ALKALOIDS - ADDITION OF CARBON NUCLEOPHILES TO N-ALKYLPYRIDINIUM SALTS [J].
BOSCH, J ;
BENNASAR, ML .
SYNLETT, 1995, (06) :587-596