Convergent syntheses of the pyrrolic marine natural products lamellarin-O, lamellarin-Q, lukianol-A and some more highly oxygenated congeners

被引:94
作者
Banwell, MG [1 ]
Flynn, BL [1 ]
Hamel, E [1 ]
Hockless, DCR [1 ]
机构
[1] NCI,DBS,MOL PHARMACOL LAB,NIH,BETHESDA,MD 20892
关键词
D O I
10.1039/a606793j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The marine alkaloids lamellarin-Q 1, lamellarin-O 2 and lukianol-A 3 as well as their more highly oxygenated congeners 22 and 23 are synthesised using Stille, Suzuki and Negishi cross-coupling reactions as the key step.
引用
收藏
页码:207 / 208
页数:2
相关论文
共 25 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]   COMBRETATROPONES - HYBRIDS OF COMBRETASTATIN AND COLCHICINE - SYNTHESIS AND BIOCHEMICAL EVALUATION [J].
ANDRES, CJ ;
BERNARDO, JE ;
YAN, Q ;
HASTIE, SB ;
MACDONALD, TL .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (04) :565-570
[3]   Cyclopropyl compounds as chemical building blocks: Total syntheses of the alkaloids (-)-colchicine, imerubrine and grandirubrine [J].
Banwell, MG .
PURE AND APPLIED CHEMISTRY, 1996, 68 (03) :539-542
[4]   CONSTITUENTS OF EUPOMATIA SPECIES .7. DIENONE-PHENOL AND DIENOL-BENZENE REARRANGEMENTS IN THE EUPODIENONE-1 SERIES [J].
BOWDEN, BF ;
READ, RW ;
TAYLOR, WC .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1981, 34 (04) :799-817
[5]   N-(TRIISOPROPYLSILYL)PYRROLE - A PROGENITOR PAR EXCELLENCE OF 3-SUBSTITUTED PYRROLES [J].
BRAY, BL ;
MATHIES, PH ;
NAEF, R ;
SOLAS, DR ;
TIDWELL, TT ;
ARTIS, DR ;
MUCHOWSKI, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) :6317-6328
[6]   SYNTHESIS OF WATER-SOLUBLE SUGAR-DERIVATIVES OF COMBRETASTATIN A-4 [J].
BROWN, RT ;
FOX, BW ;
HADFIELD, JA ;
MCGOWN, AT ;
MAYALARP, SP ;
PETTIT, GR ;
WOODS, JA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (05) :577-581
[7]   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
[8]   SYNTHESIS OF BETA-ARYL SUBSTITUTED PORPHYRINS BY PALLADIUM-CATALYZED SUZUKI CROSS-COUPLING REACTIONS [J].
CHAN, KS ;
ZHOU, XA ;
AU, MT ;
TAM, CY .
TETRAHEDRON, 1995, 51 (11) :3129-3136
[9]   PHENYLPYRROLES BY SUZUKI CROSS-COUPLING AND A SYNTHESIS OF TYPE-I TETRAMETHYLTETRAPHENYLPORPHYRIN [J].
CHANG, CK ;
BAG, N .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :7030-7032
[10]  
FURSTNER A, 1995, J ORG CHEM, V60, P6637