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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 06期

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).

引用

页码：1800 / 1805

页数：6

共 21 条

[1] ENTRY INTO 6-METHOXY-D(+)-TRYPTOPHANS - STEREOSPECIFIC SYNTHESIS OF 1-BENZENESULFONYL-6-METHOXY-D(+)-TRYPTOPHAN ETHYL-ESTER
ALLEN, MS
HAMAKER, LK
LALOGGIA, AJ
COOK, JM
[J]. 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
CHENG, JF
OHIZUMI, Y
WALCHLI, MR
NAKAMURA, H
HIRATA, Y
SASAKI, T
KOBAYASHI, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (19) : 4621 - 4624
[3] WAKAYIN - A NOVEL CYTOTOXIC PYRROLOIMINOQUINONE ALKALOID FROM THE ASCIDIAN CLAVELINA SPECIES
COPP, BR
IRELAND, CM
BARROWS, LR
[J]. 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
IZAWA, T
NISHIYAMA, S
YAMAMURA, S
[J]. 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
KITA, Y
TOHMA, H
INAGAKI, M
HATANAKA, K
YAKURA, T
[J]. 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
KOBAYASHI, J
CHENG, JF
YAMAMURA, S
ISHIBASHI, M
[J]. TETRAHEDRON LETTERS, 1991, 32 (09) : 1227 - 1228
[8] PRIANOSIN-A, A NOVEL ANTILEUKEMIC ALKALOID FROM THE OKINAWAN MARINE SPONGE PRIANOS-MELANOS
KOBAYASHI, JI
CHENG, JF
ISHIBASHI, M
NAKAMURA, H
OHIZUMI, Y
HIRATA, Y
SASAKI, T
LU, H
CLARDY, J
[J]. TETRAHEDRON LETTERS, 1987, 28 (42) : 4939 - 4942
[9] REGIOSELECTIVE CLAISEN REARRANGEMENTS IN INDOLES
MOODY, CJ
[J]. 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
NISHIYAMA, S
CHENG, JF
TAO, XL
YAMAMURA, S
[J]. TETRAHEDRON LETTERS, 1991, 32 (33) : 4151 - 4154

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