An approach to total synthesis of the cylindricine B pyridoquinoline subclass of tricyclic marine ascidian alkaloids

被引:22
作者
Chao, Wenchun [1 ]
Mahajan, Yogesh R. [1 ]
Weinreb, Steven M. [1 ]
机构
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
基金
美国国家卫生研究院;
关键词
alkaloids; ring closing metathesis; hetero Diels-Alder reaction; N-acyliminium ion; nitrogen heterocycles; cycloaddition;
D O I
10.1016/j.tetlet.2006.03.195
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Employing an intramolecular N-acylketiminium ion/olefin hetero Diels-Alder reaction, and a ring closing metathesis of a vinyl chloride as pivotal steps, it is possible to directly access the pyridoquinoline tricyclic ring system of the marine alkaloids cylindrines B and J. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3815 / 3818
页数:4
相关论文
共 20 条
[1]   CYLINDRICINE-A AND CYLINDRICINE-B, NOVEL ALKALOIDS FROM THE ASCIDIAN CLAVELINA-CYLINDRICA [J].
BLACKMAN, AJ ;
LI, CP ;
HOCKLESS, DCR ;
SKELTON, BW ;
WHITE, AH .
TETRAHEDRON, 1993, 49 (38) :8645-8656
[2]  
CHAO W, 2004, THESIS PENNSYLVANIA
[3]   Ring-closing metathesis of vinyl chlorides for formation of 5-, 6- and 7-membered carbocyclic and heterocyclic systems [J].
Chao, WC ;
Meketa, ML ;
Weinreb, SM .
SYNTHESIS-STUTTGART, 2004, (12) :2058-2061
[4]   Studies of intramolecular cyclizations of n-acyliminium ions derived from acyclic ketones: Unanticipated stereochemical and structural results [J].
Chao, WC ;
Waldman, JH ;
Weinreb, SM .
ORGANIC LETTERS, 2003, 5 (16) :2915-2918
[5]   The first examples of ring-closing olefin metathesis of vinyl chlorides [J].
Chao, WC ;
Weinreb, SM .
ORGANIC LETTERS, 2003, 5 (14) :2505-2507
[6]  
CHOI EB, 1988, SYNTHESIS-STUTTGART, P792
[7]   Intramolecular Mannich reaction in the asymmetric synthesis of polysubstituted piperidines: Concise synthesis of the dendrobate alkaloid (+)-241D and its C-4 epimer [J].
Davis, FA ;
Chao, B ;
Rao, A .
ORGANIC LETTERS, 2001, 3 (20) :3169-3171
[8]   NEW PROCEDURE FOR THE DIRECT GENERATION OF TITANIUM ENOLATES - DIASTEREOSELECTIVE BOND CONSTRUCTIONS WITH REPRESENTATIVE ELECTROPHILES [J].
EVANS, DA ;
URPI, F ;
SOMERS, TC ;
CLARK, JS ;
BILODEAU, MT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8215-8216
[9]   STEREOSELECTIVE ALDOL REACTIONS OF CHLOROTITANIUM ENOLATES - AN EFFICIENT METHOD FOR THE ASSEMBLAGE OF POLYPROPIONATE-RELATED SYNTHONS [J].
EVANS, DA ;
RIEGER, DL ;
BILODEAU, MT ;
URPI, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :1047-1049
[10]   A versatile method for the synthesis of cis-2-aminomethylcyclanols [J].
Fülöp, F ;
Simon, L ;
Simon-Talpas, G ;
Bernáth, G .
SYNTHETIC COMMUNICATIONS, 1998, 28 (12) :2303-2309