Short and flexible route to 3,4-diarylpyrrole marine alkaloids: syntheses of permethyl storniamide A, ningalin B, and lamellarin G trimethyl ether

被引：86
作者：
Iwao, M
Takeuchi, T
Fujikawa, N
Fukuda, T
Ishibashi, F
机构：
[1] Nagasaki Univ, Fac Engn, Dept Appl Chem, Nagasaki 8528521, Japan
[2] Nagasaki Univ, Div Marine Life Sci & Biochem, Nagasaki 8528521, Japan
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 24期
关键词：
D O I：
10.1016/S0040-4039(03)01031-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly efficient route to 3,4-diarylpyrrole marine alkaloids has been developed using Hinsberg-type pyrrole synthesis and palladium-catalyzed Suzuki cross-coupling of the 3,4-dihydroxypyrrole bis-triflate derivatives as key reactions. Based oil this approach. formal syntheses of permethyl storniamide A and ningalin B, and a total synthesis of lamellarin G trimethyl ether have been achieved. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：4443 / 4446
页数：4
相关论文
共 49 条
[1]   METABOLITIES OF THE MARINE PROSOBRANCH MOLLUSK LAMELLARIA SP [J].
ANDERSEN, RJ ;
FAULKNER, DJ ;
HE, CH ;
VANDUYNE, GD ;
CLARDY, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (19) :5492-5495
[2]   Convergent total synthesis of lamellarin K [J].
Banwell, M ;
Flynn, B ;
Hockless, D .
CHEMICAL COMMUNICATIONS, 1997, (23) :2259-2260
[3]   Assessment of double-barrelled heck cyclizations as a means for construction of the 14-phenyl-8,9-dihydro-6H-[1]benzopyrano[4′,3′:4,5]pyrrolo[2,1-a]isoquinolin-6-one core associated with certain members of the lamellarin class of marine natural product [J].
Banwell, MG ;
Flynn, BL ;
Hockless, DCR ;
Longmore, RW ;
Rae, AD .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1999, 52 (08) :755-765
[4]   Convergent syntheses of the pyrrolic marine natural products lamellarin-O, lamellarin-Q, lukianol-A and some more highly oxygenated congeners [J].
Banwell, MG ;
Flynn, BL ;
Hamel, E ;
Hockless, DCR .
CHEMICAL COMMUNICATIONS, 1997, (02) :207-208
[5]   Total synthesis of ningalin B utilizing a heterocyclic azadiene Diels-Alder reaction and discovery of a new class of potent multidrug resistant (MDR) reversal agents [J].
Boger, DL ;
Soenen, DR ;
Boyce, CW ;
Hedrick, MP ;
Jin, Q .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (08) :2479-2483
[6]   Total syntheses of ningalin A, lamellarin O, lukianol A, and permethyl storniamide A utilizing heterocyclic azadiene Diels-Alder reactions [J].
Boger, DL ;
Boyce, CW ;
Labroli, MA ;
Sehon, CA ;
Jin, Q .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (01) :54-62
[7]   Regioselective preparation of 2-substituted 3,4-diaryl pyrroles: A concise total synthesis of ningalin B [J].
Bullington, JL ;
Wolff, RR ;
Jackson, PF .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (26) :9439-9442
[8]   STUDIES OF AUSTRALIAN ASCIDIANS .1. 6 NEW LAMELLARIN-CLASS ALKALOIDS FROM A COLONIAL ASCIDIAN, DIDEMNUM-SP [J].
CARROLL, AR ;
BOWDEN, BF ;
COLL, JC .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1993, 46 (04) :489-501
[9]   Synthetic studies towards ML-3000 - A concise synthesis of this non-steroidal anti-inflammatory drug [J].
Cossy, J ;
Belotti, D .
TETRAHEDRON, 1999, 55 (16) :5145-5156
[10]   New lamellarin alkaloids from the Australian ascidian, Didemnum chartaceum [J].
Davis, RA ;
Carroll, AR ;
Pierens, GK ;
Quinn, RJ .
JOURNAL OF NATURAL PRODUCTS, 1999, 62 (03) :419-424
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