Synthesis of the tricyclic core of halichlorine

被引:19
作者
Hayakawa, I
Arimoto, H [1 ]
Uemura, D
机构
[1] Nagoya Univ, Grad Sch Sci, Dept Chem, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[2] Nagoya Univ, Inst Adv Res, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[3] JST, PRESTO, Chikusa Ku, Nagoya, Aichi 4648602, Japan
关键词
D O I
10.1039/b402130d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Synthesis of the tricyclic core of halichlorine, a VCAM-1 expression suppressor, was achieved using ene-yne metathesis cyclization as a key step.
引用
收藏
页码:1222 / 1223
页数:2
相关论文
共 36 条
[11]   ORGANOSELENIUM CHEMISTRY - FACILE ONE-STEP SYNTHESIS OF ALKYL ARYL SELENIDES FROM ALCOHOLS [J].
GRIECO, PA ;
GILMAN, S ;
NISHIZAWA, M .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (08) :1485-1486
[12]  
Hayakawa I, 2003, HETEROCYCLES, V59, P441
[13]   N-bromosuccinimide promoted ring expansion reactions:: Diastereoselective formation of functionalized azaspirocyclic cyclopentanones [J].
Hurley, PB ;
Dake, GR .
SYNLETT, 2003, (14) :2131-2134
[14]   Apoptosis-inducing activity of synthetic intermediates of hatichlorine [J].
Itoh, M ;
Kuwahara, J ;
Itoh, K ;
Fukuda, Y ;
Kohya, M ;
Shindo, M ;
Shishido, K .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (16) :2069-2072
[15]   Studies on the synthesis of pinnaic acid and halichlorine.: Stereoselective preparation of a (Z)-δ-chloro-γ,δ-unsaturated-β-keto phosphonate as a side chain synthon [J].
Keen, SP ;
Weinreb, SM .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (19) :6739-6741
[16]   Catalytic ring closing metathesis of dienynes: Construction of fused bicyclic [nm0] rings [J].
Kim, SH ;
Zuercher, WJ ;
Bowden, NB ;
Grubbs, RH .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (03) :1073-1081
[17]   Total synthesis of (-)-stemoamide using ruthenium-catalyzed enyne metathesis reaction [J].
Kinoshita, A ;
Mori, M .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) :8356-8357
[18]   CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].
KOLB, HC ;
VANNIEUWENHZE, MS ;
SHARPLESS, KB .
CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547
[19]   An in situ iminium formation-allylation approach towards the 1-aza-[4.5.0]-spirobicyclic core of halichlorine and pinnaic acid [J].
Koviach, JL ;
Forsyth, CJ .
TETRAHEDRON LETTERS, 1999, 40 (49) :8529-8532
[20]   Halichlorine, an inhibitor of VCAM-1 induction from the marine sponge Halichondria okadai Kadota [J].
Kuramoto, M ;
Tong, C ;
Yamada, K ;
Chiba, T ;
Hayashi, Y ;
Uemura, D .
TETRAHEDRON LETTERS, 1996, 37 (22) :3867-3870