An improved synthesis of (-)-martinellic acid via radical addition - Cyclization-elimination reaction of chiral oxime ether

被引:33
作者
Miyata, O [1 ]
Shirai, A [1 ]
Yoshino, S [1 ]
Takeda, Y [1 ]
Sugiura, M [1 ]
Naito, T [1 ]
机构
[1] Kobe Pharmaceut Univ, Higashinada Ku, Kobe, Hyogo 6588558, Japan
关键词
martinellic acid; radical reaction; oxime ether; asymmetric synthesis; pyrroloquinoline;
D O I
10.1055/s-2006-939046
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise formal synthesis of (-)-martinellic acid has been accomplished by preparing optically active dipyrroloquinoline as a key synthetic intermediate, which was prepared via the radical addition-cyclization-elimination of oxime ether carrying all unsaturated ester followed by two chemoselective reductions of the carbonyl groups.
引用
收藏
页码:893 / 896
页数:4
相关论文
共 34 条
[1]   Multi-component coupling reactions:: synthesis of a guanidine containing analog of the hexahydropyrrolo[3,2-c] quinoline alkaloid martinelline [J].
Batey, RA ;
Powell, DA .
CHEMICAL COMMUNICATIONS, 2001, (22) :2362-2363
[2]   Palladium-catalyzed aryl-amidation.: Synthesis of non-racemic N-aryl lactams [J].
Browning, RG ;
Badarinarayana, V ;
Mahmud, H ;
Lovely, CJ .
TETRAHEDRON, 2004, 60 (02) :359-365
[3]  
DANISHEFSKY S, 1975, J ORG CHEM, V40, P3807, DOI 10.1021/jo00913a053
[4]   Cyclizations of substituted benzylidene-3-alkenylamines:: Synthesis of the tricyclic core of the martinellines [J].
Frank, KE ;
Aubé, J .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (03) :655-666
[5]  
Gurjar MK, 1997, HETEROCYCLES, V45, P231
[6]   Synthesis of the heterocyclic core of the alkaloids martinelline and martinellic acid [J].
Hadden, M ;
Nieuwenhuyzen, M ;
Osborne, D ;
Stevenson, PJ ;
Thompson, N .
TETRAHEDRON LETTERS, 2001, 42 (36) :6417-6419
[7]   Regioselective synthesis of pyrroloquinolines - Approaches to martinelline. [J].
Hadden, M ;
Stevenson, PJ .
TETRAHEDRON LETTERS, 1999, 40 (06) :1215-1218
[8]   Synthesis and reactivity of hexahydropyrroloquinolines [J].
Hadden, M ;
Nieuwenhuyzen, M ;
Potts, D ;
Stevenson, PJ ;
Thompson, N .
TETRAHEDRON, 2001, 57 (26) :5615-5624
[9]   Asymmetric synthesis of tetrahydroquinoline derivative, a building block of martinellines, via intramolecular allylic amination using 9-PBN [J].
Hamada, Y ;
Kunimune, Y ;
Hara, O .
HETEROCYCLES, 2002, 56 (1-2) :97-100
[10]   Synthetic studies on bradykinin antagonist martinellines:: construction of a pyrrolo[3,2-c]quinoline skeleton using silicon-tether RCM reaction and allylic amination [J].
Hara, O ;
Sugimoto, K ;
Hamada, Y .
TETRAHEDRON, 2004, 60 (42) :9381-9390