Asymmetric synthesis of quinolizidine alkaloids (-)-lasubine I, (-)-lasubine II and (+)-subcosine II

被引：65

作者：

Chalard, P ^{[1
]}

Remuson, R ^{[1
]}

Gelas-Mialhe, Y ^{[1
]}

Gramain, JC ^{[1
]}

机构：

[1] Univ Blaise Pascal, Lab Chim Subst Nat, UMR 6504, F-63177 Aubiere, France

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 24期

关键词：

D O I：

10.1016/S0957-4166(98)00468-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The enantioselective synthesis of (-)-lasubine I 1 and the first asymmetric synthesis of (-)-lasubine II 2 and (+)-subcosine II 3 is described. The key step is the intramolecular cyclization of N-acyliminium ion 4 which is derived from (S)-aminoester 6. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4361 / 4368

页数：8

共 27 条

[1] Bardot V, 1998, HETEROCYCLES, V48, P507
[2] HIGHLY DIASTEREOSELECTIVE FORMATION OF SUBSTITUTED INDOLIZIDINES AND QUINOLIZIDINES BY RADICAL CYCLIZATION
BECKWITH, ALJ
JOSEPH, SP
MAYADUNNE, RTA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) : 4198 - 4199
[3] A HIGHLY STEREOCONTROLLED, 4-STEP SYNTHESIS OF (+/-)-LASUBINE-II
BROWN, JD
FOLEY, MA
COMINS, DL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) : 7445 - 7447
[4] BUNELLE WH, 1990, ORG SYNTH, V69, P89
[5] ENANTIOMERIC ANALYSIS IN A POLYPEPTIDE LYOTROPIC LIQUID-CRYSTAL BY DEUTERIUM NMR
CANET, I
COURTIEU, J
LOEWENSTEIN, A
MEDDOUR, A
PECHINE, JM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (24) : 6520 - 6526
[6] ENANTIOPURE 2,3-DIHYDRO-4-PYRIDONES AS SYNTHETIC INTERMEDIATES - ASYMMETRIC SYNTHESES OF THE QUINOLIZIDINE ALKALOIDS (+)-MYRTINE, (-)-LASUBINE-I, AND (+)-SUBCOSINE-I
COMINS, DL
LAMUNYON, DH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) : 5807 - 5809
[7] ASYMMETRIC-SYNTHESIS OF R-BETA-AMINO BUTANOIC ACID AND S-BETA-TYROSINE - HOMOCHIRAL LITHIUM AMIDE EQUIVALENTS FOR MICHAEL ADDITIONS TO ALPHA,BETA-UNSATURATED ESTERS
DAVIES, SG
ICHIHARA, O
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (03) : 183 - 186
[8] ELBEIN AD, 1987, ALKALOIDS CHEM BIOL, V5, pCH1
[9] ENT H, 1988, HETEROCYCLES, V27, P237
[10] FUJI K, 1978, CHEM PHARM BULL, V26, P2515

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