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

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 06期

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

页码：943 / 950

页数：8

共 53 条

[1] A straightforward synthesis of (-)-phaseolinic acid [J].

Amador, M ;

Ariza, X ;

Garcia, J ;

Ortiz, J .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) :8172-8175

[2]

Ariza X, 2001, SYNLETT, P120

[3] Asymmetric carbolithiation of 2-phenylselenofumarate derivatives: a short synthesis of (-)-roccellaric acid [J].

Bella, M ;

Margarita, R ;

Orlando, C ;

Orsini, M ;

Parlanti, L ;

Piancatelli, G .

TETRAHEDRON LETTERS, 2000, 41 (04) :561-565

[4] Enantioselective synthesis of (-)-roccellaric acid [J].

Böhm, C ;

Reiser, O .

ORGANIC LETTERS, 2001, 3 (09) :1315-1318

[5] Synthesis of natural α-methylene butyrolactones via tungsten-π-allyl complexes.: Total synthesis of (-)-methylenolactocin [J].

Chandrasekharam, M ;

Liu, RS .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) :9122-9124

[6] Enantioselective synthesis of paraconic acids [J].

Chhor, RB ;

Nosse, B ;

Sörgel, S ;

Böhn, C ;

Seitz, M ;

Reiser, O .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (01) :260-270

[7]

CHHOR RB, 2005, TOP CURR CHEM, V243, P43

[8]

CLAY RJ, 1993, SYNTHESIS-STUTTGART, P290

[9] Synthesis and molecular modeling studies of SYNPHOS®, a new, efficient diphosphane ligand for ruthenium-catalyzed asymmetric hydrogenation [J].

de Paule, SD ;

Jeulin, S ;

Ratovelomanana-Vidal, V ;

Genêt, JP ;

Champion, N ;

Dellis, P .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (10) :1931-1941

[10] SYNPHOS:: A new atropisomeric diphosphine ligand.: From laboratory-scale synthesis to scale-up development [J].

de Paule, SD ;

Jeulin, S ;

Ratovelomanana-Vidal, V ;

Genêt, JP ;

Champion, N ;

Deschaux, G ;

Dellis, P .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2003, 7 (03) :399-406

← 1 2 3 4 5 6 →