Pyrroloiminoquinone alkaloids: Discorhabdins and makaluvamines

被引：45
作者：
Harayama, Y [1 ]
Kita, Y [1 ]
机构：
[1] Osaka Univ, Grad Sch Pharmaceut Sci, Osaka, Japan
来源：
CURRENT ORGANIC CHEMISTRY | 2005年 / 9卷 / 15期
关键词：
D O I：
10.2174/138527205774370568
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The pyrroloiminoquinone alkaloid family consisting of discorhabdins and makaluvamines exhibits antitumor activities derived from their unique highly-fused structures. The total synthesis of them and the key reactions used in the total synthesis of these compounds are described.
引用
收藏
页码：1567 / 1588
页数：22
相关论文
共 47 条
[11]   Discorhabdins S, T, and U, new cytotoxic pyrroloiminoquinones from a deep-water Caribbean sponge of the genus Batzella [J].
Gunasekera, SP ;
Zuleta, IA ;
Longley, RE ;
Wright, AE ;
Pomponi, SA .
JOURNAL OF NATURAL PRODUCTS, 2003, 66 (12) :1615-1617
[12]   Discorhabdin P, a new enzyme inhibitor from a deep-water Caribbean sponge of the genus Batzella [J].
Gunasekera, SP ;
McCarthy, PJ ;
Longley, RE ;
Pomponi, SA ;
Wright, AE ;
Lobkovsky, E ;
Clardy, J .
JOURNAL OF NATURAL PRODUCTS, 1999, 62 (01) :173-175
[13]   New synthetic approach to pyrroloiminoquinone marine alkaloids. Total synthesis of makaluvamines A, D, I, and K [J].
Iwao, M ;
Motoi, O ;
Fukuda, T ;
Ishibashi, F .
TETRAHEDRON, 1998, 54 (31) :8999-9010
[14]  
Kita Y, 1999, CHEM PHARM BULL, V47, P241
[15]   Hypervalent iodine(III) induced intramolecular cyclization of substituted phenol ethers bearing an alkyl azido sidechain - A novel synthesis of quinone imine ketals [J].
Kita, Y ;
Egi, M ;
Okajima, A ;
Ohtsubo, M ;
Takada, T ;
Tohma, H .
CHEMICAL COMMUNICATIONS, 1996, (13) :1491-1492
[16]   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
[17]   NOVEL AND DIRECT NUCLEOPHILIC SULFENYLATION AND THIOCYANATION OF PHENOL ETHERS USING A HYPERVALENT IODINE(III) REAGENT [J].
KITA, Y ;
TAKADA, T ;
MIHARA, S ;
WHELAN, BA ;
TOHMA, H .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) :7144-7148
[18]   A SYNTHETIC APPROACH TO DISCORHABDIN ALKALOIDS - HYPERVALENT IODINE OXIDATION OF PARA-SUBSTITUTED PHENOL DERIVATIVES TO AZACARBOCYCLIC SPIRODIENONES [J].
KITA, Y ;
YAKURA, T ;
TOHMA, H ;
KIKUCHI, K ;
TAMURA, Y .
TETRAHEDRON LETTERS, 1989, 30 (09) :1119-1120
[19]   Total synthesis of sulfur-containing pyrroloiminoquinone marine product, (±)-makaluvamine F using hypervalent iodine(III)-induced reactions [J].
Kita, Y ;
Egi, M ;
Tohma, H .
CHEMICAL COMMUNICATIONS, 1999, (02) :143-144
[20]   Novel and efficient synthesis of sulfur-containing heterocycles using a hypervalent iodine(III) reagent [J].
Kita, Y ;
Egi, M ;
Ohtsubo, M ;
Saiki, T ;
Takada, T ;
Tohma, H .
CHEMICAL COMMUNICATIONS, 1996, (19) :2225-2226
12345