EFFICIENT SYNTHESES OF THE MARINE ALKALOIDS MAKALUVAMINE-D AND DISCORHABDIN-C - THE 4,6,7-TRIMETHOXYINDOLE APPROACH

被引:83
作者
SADANANDAN, EV [1 ]
PILLAI, SK [1 ]
LAKSHMIKANTHAM, MV [1 ]
BILLIMORIA, AD [1 ]
CULPEPPER, JS [1 ]
CAVA, MP [1 ]
机构
[1] UNIV ALABAMA,DEPT CHEM,TUSCALOOSA,AL 35487
关键词
D O I
10.1021/jo00111a043
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new and efficient synthesis of the tricyclic quinonimine 20 as its trifluoroacetate 23 has been developed starting from the commercially available 2,4,5-trimethoxybenzaldehyde and proceeding via the hitherto unknown 4,6,7-trimethoxyindole (7). Quinonimine 23 is the late stage key intermediate in several previously reported syntheses of the biologically active pyrrolo[4,3,2-de]-quinoline marine alkaloids discorhabdin C (1) and makaluvamine D (3).
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页码:1800 / 1805
页数:6
相关论文
共 21 条
[1]   ENTRY INTO 6-METHOXY-D(+)-TRYPTOPHANS - STEREOSPECIFIC SYNTHESIS OF 1-BENZENESULFONYL-6-METHOXY-D(+)-TRYPTOPHAN ETHYL-ESTER [J].
ALLEN, MS ;
HAMAKER, LK ;
LALOGGIA, AJ ;
COOK, JM .
SYNTHETIC COMMUNICATIONS, 1992, 22 (14) :2077-2102
[2]   PRIANOSIN-B, PRIANOSIN-C, AND PRIANOSIN-D NOVEL SULFUR-CONTAINING ALKALOIDS WITH POTENT ANTINEOPLASTIC ACTIVITY FROM THE OKINAWAN MARINE SPONGE PRIANOS-MELANOS [J].
CHENG, JF ;
OHIZUMI, Y ;
WALCHLI, MR ;
NAKAMURA, H ;
HIRATA, Y ;
SASAKI, T ;
KOBAYASHI, J .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (19) :4621-4624
[3]   WAKAYIN - A NOVEL CYTOTOXIC PYRROLOIMINOQUINONE ALKALOID FROM THE ASCIDIAN CLAVELINA SPECIES [J].
COPP, BR ;
IRELAND, CM ;
BARROWS, LR .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (15) :4596-4597
[4]   TOTAL SYNTHESES OF MAKALUVAMINE-A, MAKALUVAMINE-B, MAKALUVAMINE-C AND MAKALUVAMINE-D METABOLITES OF THE FIJIAN SPONGE ZYZZA CF MARSAILIS EXHIBITING INHIBITORY ACTIVITIES AGAINST TOPOISOMERASE- II [J].
IZAWA, T ;
NISHIYAMA, S ;
YAMAMURA, S .
TETRAHEDRON LETTERS, 1994, 35 (06) :917-918
[5]   TOTAL SYNTHESIS OF DISCORHABDIN-C - A GENERAL AZA SPIRO DIENONE FORMATION FROM O-SILYLATED PHENOL DERIVATIVES USING A HYPERVALENT IODINE REAGENT [J].
KITA, Y ;
TOHMA, H ;
INAGAKI, M ;
HATANAKA, K ;
YAKURA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) :2175-2180
[6]  
KNITTEL D, 1985, SYNTHESIS-STUTTGART, P186
[7]   REVISED STRUCTURES OF PRIANOSIN-C AND PRIANOSIN-D, ANTINEOPLASTIC ALKALOIDS FROM THE OKINAWAN MARINE SPONGE PRIANOS-MELANOS [J].
KOBAYASHI, J ;
CHENG, JF ;
YAMAMURA, S ;
ISHIBASHI, M .
TETRAHEDRON LETTERS, 1991, 32 (09) :1227-1228
[8]   PRIANOSIN-A, A NOVEL ANTILEUKEMIC ALKALOID FROM THE OKINAWAN MARINE SPONGE PRIANOS-MELANOS [J].
KOBAYASHI, JI ;
CHENG, JF ;
ISHIBASHI, M ;
NAKAMURA, H ;
OHIZUMI, Y ;
HIRATA, Y ;
SASAKI, T ;
LU, H ;
CLARDY, J .
TETRAHEDRON LETTERS, 1987, 28 (42) :4939-4942
[9]   REGIOSELECTIVE CLAISEN REARRANGEMENTS IN INDOLES [J].
MOODY, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (06) :1333-1337
[10]   SYNTHETIC STUDIES ON NOVEL SULFUR-CONTAINING ALKALOIDS, PRIANOSINS AND DISCORHABDINS - TOTAL SYNTHESIS OF DISCORHABDIN-C [J].
NISHIYAMA, S ;
CHENG, JF ;
TAO, XL ;
YAMAMURA, S .
TETRAHEDRON LETTERS, 1991, 32 (33) :4151-4154