Enantioselective synthesis of indolizidine and quinolizidine derivatives from chiral non-racemic bicyclic lactams

被引：40

作者：

Agami, C ^{[1
]}

Dechoux, L ^{[1
]}

Hebbe, S ^{[1
]}

Ménard, C ^{[1
]}

机构：

[1] Univ Paris 06, Lab Synth Asymetr, UMR 7611, F-75005 Paris, France

来源：

TETRAHEDRON | 2004年 / 60卷 / 25期

关键词：

bicyclic lactams; lupinine; epitashiromine; quinolizidine; indolizidine;

D O I：

10.1016/j.tet.2004.04.055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral non-racemic bicyclic lactams 2b,c, derived from (R)- and (S)-phenylglycinol, were used in the enantioselective synthesis of (-)-lupinine and 5 -epitashiromine, respectively. The efficiency of the synthesis relied on the high diastereoselectivities of formation and reduction of compounds 2b,c. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：5433 / 5438

页数：6

共 36 条

[11]

Boiteau L, 1998, ANGEW CHEM INT EDIT, V37, P1128, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1128::AID-ANIE1128>3.0.CO

[12]

2-P

[13] TOTAL SYNTHESIS OF (+/-)-MATRINE [J].

CHEN, J ;

BROWNE, LJ ;

GONNELA, NC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (12) :905-907

[14] N-ACYLDIHYDROPYRIDONES AS SYNTHETIC INTERMEDIATES - A SHORT SYNTHESIS OF (+/-)-INDOLIZIDINE-209B [J].

COMINS, DL ;

ZELLER, E .

TETRAHEDRON LETTERS, 1991, 32 (42) :5889-5892

[15]

Cordell, 2000, ALKALOIDS CHEM BIOL, V54

[16] ASYMMETRIC-SYNTHESIS FROM PYRIDINES - USE OF NEW CHIRAL 1,4-DIHYDROPYRIDINES IN A SHORT SYNTHESIS OF 5,8-DISUBSTITUTED INDOLIZIDINE (+)-209B [J].

GNECCO, D ;

MARAZANO, C ;

DAS, BC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (09) :625-626

[17] Chiral non-racemic bicyclic lactams. Auxiliary-based asymmetric reactions [J].

Groaning, MD ;

Meyers, AI .

TETRAHEDRON, 2000, 56 (51) :9843-9873

[18]

Ha DC, 1998, B KOR CHEM SOC, V19, P728

[19] ENAMINE CHEMISTRY .13. REACTION OF ALPHA,BETA-UNSATURATED ACID CHLORIDES WITH PRIMARY AND SECONDARY ENAMINES - SYNTHESIS OF TETRAHYDRO 2-OXOPYRIDINES AND OCTAHYDRO-2-OXOQUINOLINES [J].

HICKMOTT, PW ;

SHEPPARD, G .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (11) :2112-&

[20] ENAMINE CHEMISTRY .11. REACTION OF ALPHABETA-UNSATURATED ACIDS AND ACID CHLORIDES WITH IMINES - SYNTHESIS OF 2-OXOTETRAHYDROPYRIDINES AND 2-OXO-OCTAHYDROQUINOLINES [J].

HICKMOTT, PW ;

SHEPPARD, G .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (07) :1358-&

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