Synthesis of ansa-bridged macrocyclic lactams related to the antitumor antibiotic geldanamycin by ring closing metathesis

被引:26
作者
Bach, T [1 ]
Lemarchand, A [1 ]
机构
[1] Tech Univ Munich, Lehrstuhl Organ Chem 1, D-85747 Garching, Germany
关键词
arenes; antitumor agents; macrocycles; metathesis; ring closure;
D O I
10.1055/s-2002-32958
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The alpha,beta,gamma,delta-unsaturated 2,4,5-trimethoxyanilides 8a-e which bear a terminal alkenyl side chain at the 3-position were prepared from 1,2,4-trimethoxybenzene (2) in four step, and 25-41% overall yield. Attempted ring closing metathesis reactions were successful in the presence of catalysts 9 for the substrates 8c-e and led to the products 10c-e (66-91% yield). Substrates Sa and 8b with a shorter alkenyl side chain did not cyclize.
引用
收藏
页码:1302 / 1304
页数:3
相关论文
共 52 条
[1]   Ruthenium carbene complexes with imidazolin-2-ylidene ligands allow the formation of tetrasubstituted cycloalkenes by RCM [J].
Ackermann, L ;
Fürstner, A ;
Weskamp, T ;
Kohl, FJ ;
Herrmann, WA .
TETRAHEDRON LETTERS, 1999, 40 (26) :4787-4790
[2]   Synthesis of the left-hand portion of geldanamycin using an anti glycolate aldol reaction [J].
Andrus, MB ;
Meredith, EL ;
Sekhar, BBVS .
ORGANIC LETTERS, 2001, 3 (02) :259-262
[3]   Asymmetric total synthesis of halicholactone [J].
Baba, Y ;
Saha, G ;
Nakao, S ;
Iwata, C ;
Tanaka, T ;
Ibuka, T ;
Ohishi, H ;
Takemoto, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) :81-88
[4]   TOTAL SYNTHESIS OF (+)-MACBECIN-I [J].
BAKER, R ;
CASTRO, JL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (01) :47-65
[5]   Synthesis and characterization of coronanes: Multicyclopropane-fused macrocyclic arrays [J].
Barrett, AGM ;
Hamprecht, D ;
James, RA ;
Ohkubo, M ;
Procopiou, PA ;
Toledo, MA ;
White, AJP ;
Williams, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (07) :2187-2196
[6]   Enantioselective synthesis of the tetracyclic left-hand substructure of solanoeclepin A [J].
Benningshof, JCJ ;
Blaauw, RH ;
van Ginkel, AE ;
Rutjes, FPJT ;
Fraanje, J ;
Goubitz, K ;
Schenk, H ;
Hiemstra, H .
CHEMICAL COMMUNICATIONS, 2000, (16) :1465-1466
[7]   Hsp90 & Co. - a holding for folding [J].
Buchner, J .
TRENDS IN BIOCHEMICAL SCIENCES, 1999, 24 (04) :136-141
[8]   EFFECT OF TERTIARY BASES ON O-BENZOTRIAZOLYLURONIUM SALT-INDUCED PEPTIDE SEGMENT COUPLING [J].
CARPINO, LA ;
EL-FAHAM, A .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (04) :695-698
[9]   1-HYDROXY-7-AZABENZOTRIAZOLE - AN EFFICIENT PEPTIDE COUPLING ADDITIVE [J].
CARPINO, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4397-4398
[10]  
COUTTS SJ, 1990, TETRAHEDRON LETT, V31, P4301