First total synthesis of topopyrone C

被引:22
作者
Gattinoni, Sonia [1 ]
Merlini, Lucio [1 ]
Dallavalle, Sabrina [1 ]
机构
[1] Univ Milan, Dipartimento Sci Mol Agroalimentari, I-20133 Milan, Italy
关键词
topopyrone C; synthesis; anthraquinone; topoisomerase; Marschalk reaction;
D O I
10.1016/j.tetlet.2006.11.164
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first synthesis of topopyrone C, a natural compound and inhibitor of Topoisomerase 1, has been carried out by Mars-chalk alkylation of 1-hydroxy-3,6,8-trimethoxyanthraquinone, followed by a Baker-Venkataraman chain elongation and an acidcatalyzed cyclization for the construction of the pyrone ring. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1049 / 1051
页数:3
相关论文
共 19 条
[1]   Molecular rearrangement of some o-acyloxyacetophenones and the mechanism of the production of 3-acylchromones [J].
Baker, W .
JOURNAL OF THE CHEMICAL SOCIETY, 1933, :1381-1389
[2]  
BBADHWAR IC, 1932, J CHEM SOC, P1107
[3]  
CHEN AY, 1994, ANN REV PHARM TOXICO, V94, P194
[4]  
HSIANG YH, 1985, J BIOL CHEM, V260, P4873
[5]   Pyridinium chlorochromate catalyzed oxidation of alcohols to aldehydes and ketones with periodic acid [J].
Hunsen, M .
TETRAHEDRON LETTERS, 2005, 46 (10) :1651-1653
[6]   Novel human topoisomerase I inhibitors, topopyrones A, B, C and D - II. Structure elucidation [J].
Ishiyama, D ;
Kanai, Y ;
Senda, H ;
Iwatani, W ;
Takahashi, H ;
Konno, H ;
Kanazawa, S .
JOURNAL OF ANTIBIOTICS, 2000, 53 (09) :873-878
[7]   Novel human topoisomerase I inhibitors, topopyrones A, B, C and D - I. Producing strain, fermentation, isolation, physico-chemical properties and biological activity [J].
Kanai, Y ;
Ishiyama, D ;
Senda, H ;
Iwatani, W ;
Takahashi, H ;
Konno, H ;
Tokumasu, S ;
Kanazawa, S .
JOURNAL OF ANTIBIOTICS, 2000, 53 (09) :863-872
[8]   Total synthesis of premithramycinone H and related anthrapyran antibiotics [J].
Krohn, K ;
Vitz, J .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (01) :209-219
[9]  
KROHN K, 1979, LIEBIGS ANN CHEM, P19
[10]  
Marschalk C., 1936, Bull. Soc. Chim. Fr., V3, P1545