Double reductive cyclization: a facile synthesis of the indoloquinoline alkaloid cryptotackieine

被引:46
作者
Parvatkar, P. T.
Parameswaran, P. S. [1 ]
Tilve, S. G.
机构
[1] Natl Inst Oceanog, Panaji 403207, Goa, India
[2] Goa Univ, Dept Chem, Taleigao Plateau 403206, Goa, India
关键词
indoloquinoline alkaloid; Perkin reaction; cryptotackicieine; neocryptolepine; tandem; reductive cyclization;
D O I
10.1016/j.tetlet.2007.08.126
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new synthesis of the indoloquinoline alkaloid cryptotackieine, isolated from Cryptolepis sanguinolenta, is described which involves a Perkin reaction, a tandem double reduction-double cyclization reaction followed by regioselective methylation at the quinoline nitrogen. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7870 / 7872
页数:3
相关论文
共 21 条
[1]   Probing the N-5 region of the indoloquinoline alkaloid, cryptolepine for anticryptococcal activity [J].
Ablordeppey, SY ;
Fan, PC ;
Clark, AM ;
Nimrod, A .
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (02) :343-349
[2]   Formal total synthesis of the alkaloid cryptotackieine (neocryptolepine) [J].
Alajarin, M ;
Molina, P ;
Vidal, A .
JOURNAL OF NATURAL PRODUCTS, 1997, 60 (07) :747-748
[3]   New synthesis of benzo-δ-carbolines, cryptolepines, and their salts:: In vitro cytotoxic, antiplasmodial, and antitrypanosomal activities of δ-caribolines, benzo-δ-carbolines, and cryptolepines [J].
Arzel, E ;
Rocca, P ;
Grellier, P ;
Labaeïd, M ;
Frappier, F ;
Guéritte, F ;
Gaspard, C ;
Marsais, F ;
Godard, A ;
Quéguiner, G .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (06) :949-960
[4]   Ethnobotanical-directed discovery of the antihyperglycemic properties of cryptolepine:: Its isolation from Cryptolepis sanguinolenta, synthesis, and in vitro and in vivo activities [J].
Bierer, DE ;
Fort, DM ;
Mendez, CD ;
Luo, J ;
Imbach, PA ;
Dubenko, LG ;
Jolad, SD ;
Gerber, RE ;
Litvak, J ;
Lu, Q ;
Zhang, PS ;
Reed, MJ ;
Waldeck, N ;
Bruening, RC ;
Noamesi, BK ;
Hector, RF ;
Carlson, TJ ;
King, SR .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (06) :894-901
[5]   Synthesis and anticancer evaluation of certain indolo(2,3-b]quinoline derivatives [J].
Chen, YL ;
Hung, HM ;
Lu, CM ;
Li, KC ;
Tzeng, CC .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (24) :6539-6546
[6]   New alkaloids from Cryptolepis sanguinolenta [J].
Cimanga, K ;
DeBruyne, T ;
Pieters, L ;
Claeys, M ;
Vlietinck, A .
TETRAHEDRON LETTERS, 1996, 37 (10) :1703-1706
[7]   In vitro and in vivo antiplasmodial activity of cryptolepine and related alkaloids from Cryptolepis sanguinolenta [J].
Cimanga, K ;
DeBruyne, T ;
Pieters, L ;
Vlietinck, AJ .
JOURNAL OF NATURAL PRODUCTS, 1997, 60 (07) :688-691
[8]   Antibacterial and antifungal activities of neocryptolepine, biscryptolepine and cryptoquindoline, alkaloids isolated from Cryptolepis sanguinolenta [J].
Cimanga, K ;
De Bruyne, T ;
Pieters, L ;
Totte, J ;
Tona, L ;
Kambu, K ;
Vanden Berghe, D ;
Vlietinck, AJ .
PHYTOMEDICINE, 1998, 5 (03) :209-214
[9]   In vitro biological activities of alkaloids from Cryptolepis sanguinolenta [J].
Cimanga, K ;
DeBruyne, T ;
Lasure, A ;
VanPoel, B ;
Pieters, L ;
Claeys, M ;
VandenBerghe, D ;
Kambu, K ;
Tona, L ;
Vlietinck, AJ .
PLANTA MEDICA, 1996, 62 (01) :22-27
[10]   Heteroatom directed photoannulation: synthesis of indoloquinoline alkaloids: cryptolepine, cryptotackieine, cryptosanguinolentine, and their methyl derivatives [J].
Dhanabal, T. ;
Sangeetha, R. ;
Mohan, P. S. .
TETRAHEDRON, 2006, 62 (26) :6258-6263