A Concise Asymmetric Total Synthesis of (+)-Epilupinine

被引：9

作者：

Tsutsumi, Tomohiro ^{[1
,2
]}

Karanjit, Sangita ^{[1
,2
]}

Nakayama, Atsushi ^{[1
,2
]}

Namba, Kosuke ^{[1
,2
]}

机构：

[1] Tokushima Univ, Grad Sch Pharmaceut Sci, 1-78-1 Shomachi, Tokushima, Tokushima 7708505, Japan

[2] Tokushima Univ, Res Cluster Innovat Chem Sensing, 1-78-1 Shomachi, Tokushima, Tokushima 7708505, Japan

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 08期

关键词：

HIGHLY ENANTIOSELECTIVE SYNTHESIS; DIELS-ALDER; BICYCLIC ALKALOIDS; QUINOLIZIDINYL DERIVATIVES; STEREOSELECTIVE-SYNTHESIS; (+/-)-EPILUPININE; LUPININE; PROLINE; (+/-)-LUPININE; LIGANDS;

D O I：

10.1021/acs.orglett.9b00607

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric total synthesis of (+)-epilupinine was achieved in just three steps using only commercially available common reagents. The total synthesis involved alkylations of N-nosylamide, ozone oxidation, and sequential reactions of the removal of the nosyl group, intramolecular dehydrative condensation, intramolecular Mannich reaction catalyzed by L-proline, and a reduction.

引用

页码：2620 / 2624

页数：5

共 71 条

[1] A direct stereoselective approach to trans-2,3-disubstituted piperidines:: Application in the synthesis of 2-epi-CP-99,994 and (+)-epilupinine [J].

Ahari, M'hamed ;

Perez, Amandine ;

Menant, Christine ;

Vasse, Jean-Luc ;

Szymoniak, Jan .

ORGANIC LETTERS, 2008, 10 (12) :2473-2476

[2] New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].

Ahrendt, KA ;

Borths, CJ ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244

[3] Cascade iminium ion reactions for the facile synthesis of quinolizidines.: Concise syntheses of (±)-epilupinine and (-)-epimyrtine [J].

Amorde, SM ;

Judd, AS ;

Martin, SF .

ORGANIC LETTERS, 2005, 7 (10) :2031-2033

[4] Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis [J].

Austin, JF ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) :1172-1173

[5] RE-EXAMINATION OF THE ALKALOIDS OF LUPINUS-COSENTINII [J].

BECK, AB ;

GOLDSPINK, BH ;

KNOX, JR .

JOURNAL OF NATURAL PRODUCTS, 1979, 42 (04) :385-398

[6] Pyrrolizidines, indolizidines and quinolizidines via a double reductive cyclisation protocol: concise asymmetric syntheses of (+)-trachelanthamidine, (+)-tashiromine and (+)-epilupinine [J].

Brambilla, Marta ;

Davies, Stephen G. ;

Fletcher, Ai M. ;

Roberts, Paul M. ;

Thomson, James E. ;

Zimmer, David .

TETRAHEDRON, 2016, 72 (47) :7417-7429

[7]

BUNSUPA S, FRONT PLANT SCI

[8] Novel amodiaquine congeners as potent antimalarial agents [J].

Casagrande, Manolo ;

Basilico, Nicoletta ;

Parapini, Silvia ;

Romeo, Sergio ;

Taramelli, Donatella ;

Sparatore, Anna .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (14) :6813-6823

[9] BICYCLIC BETA-ENAMINOESTERS - STEREOSPECIFIC SYNTHESIS AND REDUCTION - ROUTES TO ISORETRONECANOL, TRACHELANTHAMIDINE, LUPININE AND EPILUPININE [J].

CELERIER, JP ;

HADDAD, M ;

SALIOU, C ;

LHOMMET, G ;

DHIMANE, H ;

POMMELET, JC ;

CHUCHE, J .

TETRAHEDRON, 1989, 45 (19) :6161-6170

[10]

CHONG JM, 1995, TETRAHEDRON-ASYMMETR, V6, P409

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