Formal stereoselective synthesis of (±)-akagerine

被引:18
作者
Bennasar, ML [1 ]
Vidal, B [1 ]
Sufi, BA [1 ]
Bosch, J [1 ]
机构
[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain
关键词
D O I
10.1039/a807868h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A stereoselective synthesis of pentacyclic dilactam 1, a known precursor of the indole alkaloid akagerine, involving addition of the enolate of 1-acetylindole 2 to 3-acetyl-2-fluoropyridinium salt 3, cyclization of the resultant IP-dihydropyridine, elaboration of the (E)-ethylidene substituent and closure of the C ring by Pummerer reaction, is reported.
引用
收藏
页码:2639 / 2640
页数:2
相关论文
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