Organocatalytic enantioselective synthesis of quinolizidine alkaloids (+)-myrtine, (-)-lupinine, and (+)-epiepiquinamide

被引：33

作者：

Fustero, Santos ^{[1
,2
]}

Moscardo, Javier ^{[1
]}

Sanchez-Rosello, Maria ^{[2
]}

Flores, Sonia ^{[1
]}

Guerola, Marta ^{[1
]}

del Pozo, Carlos ^{[1
]}

机构：

[1] Univ Valencia, Dept Quim Organ, E-46100 Burjassot, Spain

[2] Ctr Invest Principe Felipe, Lab Mol Organ, E-46012 Valencia, Spain

来源：

TETRAHEDRON | 2011年 / 67卷 / 38期

关键词：

Organocatalysis; Quinolizidine alkaloids; Intramolecular aza-Michael reaction; Myrtine; Lupinine; Epiquinamide; AZA-MICHAEL REACTION; ASYMMETRIC-SYNTHESIS; CONCISE SYNTHESIS; INDOLIZIDINE; EPIQUINAMIDE; LUPININE; ACCESS; POISON;

D O I：

10.1016/j.tet.2011.07.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The organocatalytic synthesis of quinolizidine alkaloids (+)-myrtine, (-)-lupinine, and (+)-epiepiquinamide is described. It involved, as the key step, an enantioselective intramolecular aza-Michael reaction (IMAMR) catalyzed by Jorgensen catalyst I, affording the common precursor with high enantioselectivity. This compound was subsequently transformed into the three alkaloids in a highly diastereoselective manner. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：7412 / 7417

页数：6

共 52 条

[1] Enantioselective synthesis of indolizidine and quinolizidine derivatives from chiral non-racemic bicyclic lactams
Agami, C
Dechoux, L
Hebbe, S
Ménard, C
[J]. TETRAHEDRON, 2004, 60 (25) : 5433 - 5438
[2] Short Access to (+)-Lupinine and (+)-Epiquinamide via Double Hydroformylation
Airiau, Etienne
Spangenberg, Thomas
Girard, Nicolas
Breit, Bernhard
Mann, Andre
[J]. ORGANIC LETTERS, 2010, 12 (03) : 528 - 531
[3] Remote stereocenter discrimination in the enzymatic resolution of piperidine-2-ethanol. Short enantioselective synthesis of sedamine and allosedamine
Angoli, M
Barilli, A
Lesma, G
Passarella, D
Riva, S
Silvani, A
Danieli, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) : 9525 - 9527
[4] Enantioselective phase-transfer-catalyzed intramolecular Aza-Michael reaction: Effective route to pyrazino-indole compounds
Bandini, Marco
Eichholzer, Astrid
Tragni, Michele
Umani-Ronchi, Achille
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (17) : 3238 - 3241
[5] BAUMERT G, 1982, CHEM BER, V14, P634
[6] BAUMERT G, 1881, CHEM BER, V14, P1321
[7] Organocatalysis-after the gold rush
Bertelsen, Soren
Jorgensen, Karl Anker
[J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) : 2178 - 2189
[8] Enantioselective Intramolecular Aza-Michael Additions of Indoles Catalyzed by Chiral Phosphoric Acids
Cai, Quan
Zheng, Chao
You, Shu-Li
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (46) : 8666 - 8669
[9] Improved protocol for asymmetric, intramolecular heteroatom Michael addition using organocatalysis: Enantioselective syntheses of homoproline, pelletierine, and homopipecolic acid
Carlson, Erik C.
Rathbone, Lauren K.
Yang, Hua
Collett, Nathan D.
Carter, Rich G.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (13) : 5155 - 5158
[10] Stereoflexible total synthesis of (-)-epiquinamide
Chandrasekhar, S.
Parida, Bibhuti Bhusan
Rambabu, Ch.
[J]. TETRAHEDRON LETTERS, 2009, 50 (26) : 3294 - 3295

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