Synthesis of naturally occurring polyacetylenes via a bis-silylated diyne

被引:34
作者
Fiandanese, Vito [1 ]
Bottalico, Daniela [1 ]
Marchese, Giuseppe [1 ]
Punzi, Angela [1 ]
机构
[1] Univ Bari, Dipartmento Chim, I-70126 Bari, Italy
关键词
silicon and compounds; polyacetylenes; coupling reactions; bioactive products;
D O I
10.1016/j.tet.2006.03.043
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A straightforward synthesis of a series of naturally occurring polyacetylenes has been developed, including the montiporynes A C ells, the atractylodin, with antibiotic at and C, possessing cytotoxic activity against several human solid tumor c activity against Escherichia coli, and triynes, which display insecticidal activities, starting from the readily available 1,4-bis(trimethylsilyl)-1,3-butadiyne. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5126 / 5132
页数:7
相关论文
共 27 条
[1]   Cytotoxic diacetylenes from the stony coral Montipora species [J].
Alam, N ;
Bae, BH ;
Hong, JK ;
Lee, CO ;
Im, KS ;
Jung, JH .
JOURNAL OF NATURAL PRODUCTS, 2001, 64 (08) :1059-1063
[2]   New acetylenic compounds from the stony coral Montipora sp. [J].
Bae, BH ;
Im, KS ;
Choi, WC ;
Hong, JK ;
Lee, CO ;
Choi, JS ;
Son, BW ;
Song, JI ;
Jung, JH .
JOURNAL OF NATURAL PRODUCTS, 2000, 63 (11) :1511-1514
[3]  
Bohlmann F, 1973, NATURALLY OCCURRING
[4]   Molybdate-exchanged Mg-Al-LDH catalyst:: an eco-compatible route for the synthesis of β-bromostyrenes in aqueous medium [J].
Choudary, BM ;
Someshwar, T ;
Kantam, ML ;
Reddy, CV .
CATALYSIS COMMUNICATIONS, 2004, 5 (05) :215-219
[5]   Synthesis of 1-methyl-4-alkyl-1,3-diacetylenes. Prototropic rearrangement in 1-alkyl-1,3-diacetylenes [J].
Dabdoub, MJ ;
Dabdoub, VB ;
Lenardao, EJ .
TETRAHEDRON LETTERS, 2001, 42 (10) :1807-1809
[6]   Synthesis of polyacetylenic montiporic acids by means of organosilicon compounds [J].
Fiandanese, V ;
Bottalico, D ;
Marchese, G ;
Punzi, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (12) :3004-3008
[7]   Stereoselective total synthesis of (S)-Virol C and (S)-1-dehydroxyvirol A [J].
Fiandanese, V ;
Bottalico, D ;
Cardellicchio, C ;
Marchese, G ;
Punzi, A .
TETRAHEDRON, 2005, 61 (19) :4551-4556
[8]   New stereoselective methodology for the synthesis of dihydroxerulin and xerulin, potent inhibitors of the biosynthesis of cholesterol [J].
Fiandanese, V ;
Bottalico, D ;
Marchese, G ;
Punzi, A .
TETRAHEDRON, 2004, 60 (50) :11421-11425
[9]   A straightforward method for the synthesis of unsymmetrically substituted 1,3-diynes [J].
Fiandanese, V ;
Bottalico, D ;
Marchese, G ;
Punzi, A .
TETRAHEDRON LETTERS, 2003, 44 (51) :9087-9090
[10]   A new mild procedure for the direct coupling of 1-trimethylsilyl acetylenes with vinyl triflates or aryl iodide [J].
Halbes, U ;
Pale, P .
TETRAHEDRON LETTERS, 2002, 43 (11) :2039-2042