Total synthesis of (-)-martinellic acid

被引:38
作者
Badarinarayana, Vivek [1 ]
Lovely, Carl J. [1 ]
机构
[1] Univ Texas, Dept Chem & Biochem, Arlington, TX 76019 USA
基金
美国国家科学基金会;
关键词
D O I
10.1016/j.tetlet.2007.02.008
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An enantioselective formal total synthesis of the pyrrolo[3,2-c]quinoline natural product martinellic acid has been achieved. The key steps involve a Pd-catalyzed aryl amidation reaction of a pyrroglutamate derivative, an intramolecular [3+2] azomethine ylide-alkene cycloaddition and a reductive ring opening reaction. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2607 / 2610
页数:4
相关论文
共 54 条
[11]   TOTAL SYNTHESIS OF (+/-)-VERNOLEPIN AND (+/-)-VERNOMENIN [J].
GRIECO, PA ;
NISHIZAWA, M ;
BURKE, SD ;
MARINOVIC, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (06) :1612-1613
[12]   ORGANOSELENIUM CHEMISTRY - FACILE ONE-STEP SYNTHESIS OF ALKYL ARYL SELENIDES FROM ALCOHOLS [J].
GRIECO, PA ;
GILMAN, S ;
NISHIZAWA, M .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (08) :1485-1486
[13]  
Gurjar MK, 1997, HETEROCYCLES, V45, P231
[14]   Synthesis of the heterocyclic core of martinelline and martinellic acid [J].
Hadden, M ;
Nieuwenhuyzen, M ;
Osborne, D ;
Stevenson, PJ ;
Thompson, N ;
Walker, AD .
TETRAHEDRON, 2006, 62 (17) :3977-3984
[15]   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
[16]   Regioselective synthesis of pyrroloquinolines - Approaches to martinelline. [J].
Hadden, M ;
Stevenson, PJ .
TETRAHEDRON LETTERS, 1999, 40 (06) :1215-1218
[17]   Synthesis and reactivity of hexahydropyrroloquinolines [J].
Hadden, M ;
Nieuwenhuyzen, M ;
Potts, D ;
Stevenson, PJ ;
Thompson, N .
TETRAHEDRON, 2001, 57 (26) :5615-5624
[18]   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
[19]   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
[20]   New synthesis of a pyrroloquinoline skeleton, the Martinelline core, using a tandem Michael-Aldol strategy [J].
Hara, O ;
Sugimoto, K ;
Makino, K ;
Hamada, Y .
SYNLETT, 2004, (09) :1625-1627