EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .19. ELABORATION OF 2-FORMYLQUINIZARIN THROUGH A WITTIG REACTION

被引:2
作者
BONIFACE, PJ [1 ]
CAMBIE, RC [1 ]
CARROLL, DR [1 ]
MARSH, NF [1 ]
MILBANK, JBJ [1 ]
RUTLEDGE, PS [1 ]
WOODGATE, PD [1 ]
机构
[1] UNIV AUCKLAND,DEPT CHEM,PRIVATE BAG 92019,AUCKLAND,NEW ZEALAND
关键词
D O I
10.1071/CH9940441
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reaction of 2-formylquinizarin dimethyl ether (3) with the dimethoxy ylide (6) gives an alpha,beta-unsaturated ester (8) which on hydrogenation, reduction and methylation gives the tetramethoxyanthracene diester (18). When linked to work by Dotz and Popall this sequence provides a route to (+/-)-4-demethoxydaunomycinone.
引用
收藏
页码:441 / 449
页数:9
相关论文
共 50 条
[41]   SYNTHESIS AND CONVERSIONS OF BETA,GAMMA-UNSATURATED AMINES .19. REACTION OF 1,2,3,4-TETRACHLOROBUTANES WITH SECONDARY-AMINES [J].
GEGELYAN, ZG ;
MIRAKYAN, SM ;
MARTIROS.GT .
ARMYANSKII KHIMICHESKII ZHURNAL, 1974, 27 (04) :314-318
[42]   Synthesis of 6H-Isoindolo[2,1-a]indol-6-ones Through Wittig Reaction and Tandem Reductive Cyclization-Lactamization [J].
Kadam, Hari K. ;
Tilve, Santosh G. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (20) :4280-4284
[43]   SYNTHESIS OF SUBSTANCES RELATED TO GIBBERELLINS .19. FURTHER EXPERIMENTS ON TOTAL SYNTHESIS OF (+-)-GIBBERELLINS A2 A4 A9 AND A10 BIOCHEMICAL STUDIES ON BAKANAE FUNGUS .77. [J].
MORI, K ;
SHIOZAKI, M ;
MATSUI, M ;
SUMIKI, Y .
PROCEEDINGS OF THE JAPAN ACADEMY, 1968, 44 (07) :717-&
[44]   SYNTHESIS OF NUCLEOSIDES AND RELATED-COMPOUNDS .19. 3-ACETOXY-2-DIMETHYLPHOSPHONOACRYLATES - NEW DIENOPHILES AND THEIR USE FOR THE SYNTHESIS OF CARBOCYCLIC C-NUCLEOSIDE PRECURSORS BY THE AID OF RRA REACTION [J].
KATAGIRI, N ;
YAMAMOTO, M ;
KANEKO, C .
CHEMISTRY LETTERS, 1990, (10) :1855-1858
[45]   Interfacial Reaction-Directed Green Synthesis of CeO2-MnO2 Catalysts for Imine Production through Oxidative Coupling of Alcohols and Amines [J].
Li, Jingwen ;
Hu, Riming ;
Liu, Wei ;
Gao, Daowei ;
Zhao, Huaiqing ;
Li, Chunsheng ;
Jiang, Xuchuan ;
Chen, Guozhu .
INORGANIC CHEMISTRY, 2023, 62 (08) :3692-3702
[46]   Diastereoselective synthesis of 2,5-disubstituted-3-hydroxy-tetrahydrofurans through a counterion-directed Tsuji-Trost reaction [J].
Caumes, Xavier ;
Jeanne-Julien, Louis ;
Khelifi, Chakib ;
Gandon, Vincent ;
Roulland, Emmanuel .
ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (11) :1462-1466
[47]   PREPARATION OF 6,10-DIMETHYLSPIRO[4,5]DEC-6-EN-2-ONE - EXPERIMENTS DIRECTED TOWARDS SYNTHESIS OF SPIROVETIVANE SESQUITERPENES [J].
OGISO, A ;
KURABAYA.M ;
NAGAHORI, H ;
MISHIMA, H .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1970, 18 (06) :1283-+
[48]   STUDIES IN VILSMEIER-HAACK REACTION .19. SYNTHESIS OF ISOXAZOLO[3,2-B]QUINAZOLONE FROM 2-HYDROXY-3-METHYL-4-QUINAZOLONE [J].
BARNELA, SB ;
SESHADRI, S .
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1986, 25 (07) :709-711
[49]   Towards the Total Synthesis of Pl-3: Preparation of the Eastern Fragment through a Diastereoselective SmI2-Mediated Reformatsky Reaction [J].
Fuerst, Rita ;
Lentsch, Christoph ;
Rinner, Uwe .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (12) :2293-2297
[50]   EXPERIMENTS DIRECTED TOWARD TOTAL SYNTHESIS OF TERPENES .19. SYNTHESIS OF 8-METHOXY-4ABETA, 10BBETA,12AALPHA-TRIMETHYL-3,4,4A,4BALPHA,5,6,10B,11,12,12A-DECAHYDROCHRYSEN-1(2H)-ONE, A KEY INTERMEDIATE IN TOTAL SYNTHESIS OF (+ OR -)-SHIONONE [J].
IRELAND, RE ;
DAWSON, MI ;
KOWALSKI, CJ ;
LIPINSKI, CA ;
MARSHALL, DR ;
TILLEY, JW ;
BORDNER, J ;
TRUS, BL .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (08) :973-990