The first total synthesis of vinaxanthone, a fungus metabolite possessing multiple bioactivities

被引:22
作者
Tatsuta, Kuniaki [1 ]
Kasai, Soko [1 ]
Amano, Yuki [1 ]
Yamaguchi, Takahiro [1 ]
Seki, Masashi [1 ]
Hosokawa, Seijiro [1 ]
机构
[1] Waseda Univ, Sch Sci & Engn, Dept Appl Chem, Shinjuku Ku, Tokyo 1698555, Japan
关键词
PENICILLIUM; INHIBITOR; XANTHOFULVIN; DNA;
D O I
10.1246/cl.2007.10
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Vinaxanthone (1) has been biomimetically synthesized from vanillin (2) through an intermolecular Diels-Alder cycloaddition between two molecules of the precursor 11.
引用
收藏
页码:10 / 11
页数:2
相关论文
共 11 条
[1]   STRUCTURE OF A NOVEL PHOSPHOLIPASE-C INHIBITOR, VINAXANTHONE (RO-09-1450), PRODUCED BY PENICILLIUM-VINACEUM [J].
AOKI, M ;
ITEZONO, Y ;
SHIRAI, H ;
NAKAYAMA, N ;
SAKAI, A ;
TANAKA, Y ;
YAMAGUCHI, A ;
SHIMMA, N ;
YOKOSE, K ;
SETO, H .
TETRAHEDRON LETTERS, 1991, 32 (36) :4737-4740
[3]  
Fürstner A, 2002, CHEM-EUR J, V8, P1856, DOI 10.1002/1521-3765(20020415)8:8<1856::AID-CHEM1856>3.0.CO
[4]  
2-R
[5]  
HECK RF, 1982, ORG REACTIONS, V27, P345
[6]   In vitro and in vivo characterization of a novel semaphorin 3A inhibitor, SM-216289 or xanthofulvin [J].
Kikuchi, K ;
Kishino, A ;
Konishi, O ;
Kumagai, K ;
Hosotani, N ;
Saji, I ;
Nakayama, C ;
Kimura, T .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (44) :42985-42991
[7]   Xanthofulvin, a novel semaphorin inhibitor produced by a strain of Penicillium [J].
Kumagai, K ;
Hosotani, N ;
Kikuchi, K ;
Kimura, T ;
Saji, I .
JOURNAL OF ANTIBIOTICS, 2003, 56 (07) :610-616
[8]  
RAO DV, 1983, SYNTHESIS-STUTTGART, P308
[9]   A general method for the synthesis of 2′-O-cyanoethylated oligoribonucleotides having promising hybridization affinity for DNA and RNA and enhanced nuclease resistance [J].
Saneyoshi, H ;
Seio, K ;
Sekine, M .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (25) :10453-10460
[10]   ENANTIODIVERGENT TOTAL SYNTHESES OF NANAOMYCINS AND THEIR ENANTIOMERS, KALAFUNGINS [J].
TATSUTA, K ;
AKIMOTO, K ;
ANNAKA, M ;
OHNO, Y ;
KINOSHITA, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1985, 58 (06) :1699-1706