Total synthesis and absolute stereochemistry of plakortone E

被引:24
作者
Akiyama, M [1 ]
Isoda, Y [1 ]
Nishimoto, M [1 ]
Narazaki, M [1 ]
Oka, H [1 ]
Kuboki, A [1 ]
Ohira, S [1 ]
机构
[1] Okayama Univ Sci, Fac Sci, Dept Biol Chem, Okayama 7000005, Japan
关键词
plakortone E; alkylidenecarbene; C-H insertion; absolute stercochemistry;
D O I
10.1016/j.tetlet.2006.02.025
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The absolute stereochemistry of plakortone E, it cytotoxic metabolite of the Caribbean sponge, was established to be 1. by the synthesis of the racemic C-8 epimer (+/-)-2 and then of (-)-1 itself, which was identical with the natural compound. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2287 / 2290
页数:4
相关论文
共 21 条
[1]   Stereocontrolled synthesis of (±)-methyl 3,6-epoxy-4,6,8-triethyl-2,4,9-dodecatrienoate, a major metabolite of Caribbean sponge, Plakortis halichondrioides, using reactions of alkylidenecarbenes in one pot [J].
Akiyama, M ;
Isoda, Y ;
Nishimoto, M ;
Kobayashi, A ;
Togawa, D ;
Hirao, N ;
Kuboki, A ;
Ohira, S .
TETRAHEDRON LETTERS, 2005, 46 (44) :7483-7485
[2]   STEREOCONTROLLED SYNTHESIS OF A POLYETHER FRAGMENT [J].
BARTLETT, PA ;
HOLM, KH ;
MORIMOTO, A .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5179-5183
[3]   A synthetic approach to the plakortones [J].
Bittner, C ;
Burgo, A ;
Murphy, PJ ;
Sung, CH ;
Thornhill, AJ .
TETRAHEDRON LETTERS, 1999, 40 (17) :3455-3456
[4]   The modified Julia olefination:: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds [J].
Blakemore, PR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (23) :2563-2585
[5]  
Blakemore PR, 1998, SYNLETT, P26
[6]   Metabolites from the sponge Plakortis simplex.: II.: Isolation of four bioactive lactone compounds and of a novel related amino acid [J].
Cafieri, F ;
Fattorusso, E ;
Taglialatela-Scafati, O ;
Di Rosa, M ;
Ianaro, A .
TETRAHEDRON, 1999, 55 (48) :13831-13840
[7]  
CURRAN DP, 1992, SYNTHESIS-STUTTGART, P123
[8]   Isolation and biological evaluation of filiformin, plakortide F, and plakortone G from the Caribbean sponge Plakortis sp. [J].
Gochfeld, DJ ;
Hamann, MT .
JOURNAL OF NATURAL PRODUCTS, 2001, 64 (11) :1477-1479
[9]  
Hayes PY, 2004, HETEROCYCLES, V62, P173
[10]   Total synthesis and absolute stereochemistry of plakortone D [J].
Hayes, PY ;
Kitching, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (33) :9718-9719