Ruthenium-catalyzed hydrovinylation of dienoates: Model studies directed toward the c10-c18 segment of ambruticin

被引:21
作者
He, ZJ [1 ]
Yi, CS [1 ]
Donaldson, WA [1 ]
机构
[1] Univ Wisconsin, Dept Chem, Milwaukee, WI 53201 USA
关键词
ruthenium catalysis; hydrovinylation; cross-metathesis;
D O I
10.1055/s-2004-825605
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The ruthenium-catalyzed hydrovinylation of 2,4-dienoates 3 proceeds in a regioselective fashion to give 4-alkyl-2,5-dienoates 4 in good yields. Olefin cross-metathesis of a vinylcyclopropane with 4e demonstrates a synthetic route to the C10-C18 segment of ambruticin.
引用
收藏
页码:1312 / 1314
页数:3
相关论文
共 29 条
[1]  
Bösmann A, 2001, ANGEW CHEM INT EDIT, V40, P2697, DOI 10.1002/1521-3773(20010716)40:14<2697::AID-ANIE2697>3.0.CO
[2]  
2-W
[3]   INTERMEDIATES IN THE EPOXIDATION OF ALKENES BY CYTOCHROME-P-450 MODELS .2. USE OF THE TRANS-2,TRANS-3-DIPHENYLCYCLOPROPYL SUBSTITUENT IN A SEARCH FOR RADICAL INTERMEDIATES [J].
CASTELLINO, AJ ;
BRUICE, TC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) :7512-7519
[4]   A general model for selectivity in olefin cross metathesis [J].
Chatterjee, AK ;
Choi, TL ;
Sanders, DP ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11360-11370
[5]   W-7783, A UNIQUE ANTIFUNGAL ANTIBIOTIC [J].
CONNOR, DT ;
GREENOUGH, RC ;
STRANDTMANN, MV .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (23) :3664-3669
[6]   Highly enantioselective nickel-catalyzed hydrovinylation with chiral phosphoramidite ligands [J].
Franciò, G ;
Faraone, F ;
Leitner, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (05) :736-737
[7]  
Goossen LJ, 2002, ANGEW CHEM INT EDIT, V41, P3775, DOI 10.1002/1521-3773(20021018)41:20<3775::AID-ANIE3775>3.0.CO
[8]  
2-2
[9]   Regio- and stereoselective ruthenium-catalyzed hydrovinylation of 1,3-dienes:: Application to the generation of a 20(S) steroidal side chain [J].
He, ZJ ;
Yi, CS ;
Donaldson, WA .
ORGANIC LETTERS, 2003, 5 (09) :1567-1569
[10]   Synthesis of bis- and oligo-gem-difluorocyclopropanes using the olefin metathesis reaction [J].
Itoh, T ;
Mitsukura, K ;
Ishida, N ;
Uneyama, K .
ORGANIC LETTERS, 2000, 2 (10) :1431-1434