General enantioselective synthesis of butyrolactone natural products via ruthenium-SYNPHOS®-catalyzed hydrogenation reactions

被引:50
作者
Blanc, Delphine [1 ]
Madec, Jonathan [1 ]
Popowyck, Florence [1 ]
Ayad, Tahar [1 ]
Phansavath, Phannarath [1 ]
Ratovelomanana-Vidal, Virginie [1 ]
Genet, Jean-Pierre [1 ]
机构
[1] Coll France, CNRS UMR 7573, Lab Synth Select Organ & Prod Nat, F-75231 Paris 05, France
关键词
asymmetric catalysis; atropisomerism; hydrogenation; ruthenium; total synthesis;
D O I
10.1002/adsc.200600504
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Enantioselective syntheses of several paraconic acids have been achieved using catalyzed asymmetric, hydrogenation of beta-keto esters with SYNPHOS (R) as a ligand. This strategy allowed the short synthesis of biologically active (-)-methyleno-lactocin 1, (-)-protolichesterinic acid 2, (-)-phaseoconic acids have been achieved using linic acid 3 and (+)-roccellaric acid 4.
引用
收藏
页码:943 / 950
页数:8
相关论文
共 53 条
[31]   APPLICATION OF RADICAL CYCLISATION/IODINE ATOM-TRANSFER TO THE CHIRAL SYNTHESIS OF (-)-METHYLENOLACTOCIN [J].
MAWSON, SD ;
WEAVERS, RT .
TETRAHEDRON, 1995, 51 (41) :11257-11270
[32]   Stereoselective synthesis of diltiazem via dynamic kinetic resolution [J].
Mordant, C ;
de Andrade, CC ;
Touati, R ;
Ratovelomanana-Vidal, V ;
Hassine, BB ;
Genet, JP .
SYNTHESIS-STUTTGART, 2003, (15) :2405-2409
[33]  
MORDANT C, 2004, TETRAHEDRON, P2405
[34]   Facially controlled C-methylation of oxolanyl and cyclopentyl acetate enolates:: Application to the total synthesis of (+)-nephromopsinic acid [J].
Mulzer, J ;
Steffen, U ;
Martin, HJ ;
Zorn, L .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (06) :1028-1043
[35]   1ST ASYMMETRIC-SYNTHESIS OF (+)-ROCCELLARIC ACID AND (-)-ROCCELLARIC ACID AND DIHYDROPROTOLICHESTERINIC ACID [J].
MULZER, J ;
SALIMI, N ;
HARTL, H .
TETRAHEDRON-ASYMMETRY, 1993, 4 (03) :457-471
[36]   HIGHLY FELKIN-ANH SELECTIVE HIYAMA ADDITIONS OF CHIRAL ALLYLIC BROMIDES TO ALDEHYDES - APPLICATION TO THE 1ST SYNTHESIS OF NEPHROMOPSINIC ACID AND ITS ENANTIOMER [J].
MULZER, J ;
KATTNER, L ;
STRECKER, AR ;
SCHRODER, C ;
BUSCHMANN, J ;
LEHMANN, C ;
LUGER, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4218-4229
[37]   SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF (-)-PROTOLICHESTERINIC ACID, ANTITUMOR ANTIBIOTIC LACTONE FROM CETRARIA-ISLANDICA [J].
MURTA, MM ;
DEAZEVEDO, MBM ;
GREENE, AE .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) :7537-7541
[38]  
Noyori R, 2002, ANGEW CHEM INT EDIT, V41, P2008, DOI 10.1002/1521-3773(20020617)41:12<2008::AID-ANIE2008>3.0.CO
[39]  
2-4
[40]  
NOYORI R, 2000, CATALYTIC ASYMMETRIC, P1