A SHORT SYNTHESIS OF THE ANTIMICROBIAL MARINE SPONGE PIGMENT FASCAPLYSIN

被引:33
作者
ROCCA, P [1 ]
MARSAIS, F [1 ]
GODARD, A [1 ]
QUEGUINER, G [1 ]
机构
[1] INST NATL SCI APPL ROUEN,CNRS,URA 1429,CHIM ORGAN FINE & HETEROCYCL LAB,F-76131 MONT ST AIGNAN,FRANCE
关键词
ALKALOID; CROSS-COUPLING; FASCAPLYSIN; METALATION; PALLADIUM;
D O I
10.1016/S0040-4039(00)61510-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A short and convergent synthesis of Fascaplysin is reported. The approach is based on a recently developped methodology which involves such reactions as metalation, heteroring cross-coupling and cyclization.
引用
收藏
页码:7917 / 7918
页数:2
相关论文
共 9 条
[1]  
Gschwend H.W., 1976, ORG REACT NY, V26, P1
[2]   THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF PHENYLBORONIC ACID WITH HALOARENES IN THE PRESENCE OF BASES [J].
MIYAURA, N ;
YANAGI, T ;
SUZUKI, A .
SYNTHETIC COMMUNICATIONS, 1981, 11 (07) :513-519
[3]   TOTAL SYNTHESIS OF THE MARINE SPONGE PIGMENT FASCAPLYSIN [J].
PELCMAN, B ;
GRIBBLE, GW .
TETRAHEDRON LETTERS, 1990, 31 (17) :2381-2384
[4]   DIRECTED METALATION OF PI-DEFICIENT AZAAROMATICS - STRATEGIES OF FUNCTIONALIZATION OF PYRIDINES, QUINOLINES, AND DIAZINES [J].
QUEGUINER, G ;
MARSAIS, F ;
SNIECKUS, V ;
EPSZTAJN, J .
ADVANCES IN HETEROCYCLIC CHEMISTRY, 1991, 52 :187-304
[5]   CONNECTION BETWEEN METALATION AND CROSS-COUPLING STRATEGIES - A NEW CONVERGENT ROUTE TO AZACARBAZOLES [J].
ROCCA, P ;
MARSAIS, F ;
GODARD, A ;
QUEGUINER, G .
TETRAHEDRON, 1993, 49 (01) :49-64
[6]   A NEW CONVERGENT SYNTHESIS OF ALPHA-SUBSTITUTED-BETA-CARBOLINES [J].
ROCCA, P ;
MARSAIS, F ;
GODARD, A ;
QUEGUINER, G .
TETRAHEDRON, 1993, 49 (16) :3325-3342
[7]   FASCAPLYSIN, AN UNUSUAL ANTIMICROBIAL PIGMENT FROM THE MARINE SPONGE FASCAPLYSINOPSIS SP [J].
ROLL, DM ;
IRELAND, CM ;
LU, HSM ;
CLARDY, J .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14) :3276-3278
[8]   DIRECTED ORTHO METALATION - TERTIARY AMIDE AND O-CARBAMATE DIRECTORS IN SYNTHETIC STRATEGIES FOR POLYSUBSTITUTED AROMATICS [J].
SNIECKUS, V .
CHEMICAL REVIEWS, 1990, 90 (06) :879-933
[9]   IMPROVED SYNTHESIS OF 2,3-DISUBSTITUTED PYRIDINES BY METALATION OF 2-CHLOROPYRIDINE - A CONVENIENT ROUTE TO FUSED POLYHETEROCYCLES [J].
TRECOURT, F ;
MARSAIS, F ;
GUNGOR, T ;
QUEGUINER, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (09) :2409-2415