Synthesis of (-)-Cytisine Using a 6-endo aza-Michael Addition

被引：17

作者：

Barat, Viktor ^{[1
]}

Csokas, Daniel ^{[1
]}

Bates, Roderick W. ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 16期

关键词：

ENANTIOSELECTIVE SYNTHESIS; DERIVATIVES; ALKALOIDS; CYTISINE; ROUTE;

D O I：

10.1021/acs.joc.8b01156

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric synthesis of (-)-cytisine has been achieved. The piperidine C-ring was formed using a stereodivergent intramolecular 6-endo aza-Michael addition. The B-ring was established by intramolecular pyridine N-alkylation. The absolute stereochemistry was established by an Evans acyl oxazolidinone enolate alkylation reaction that proceeded with an unexpected stereochemical outcome due to participation of the pyridine nitrogen lone pair.

引用

页码：9088 / 9095

页数：8

共 29 条

[21] Mitsunobu reaction modifications allowing product isolation without chromatography: application to a small parallel library [J].

Pelletier, JC ;

Kincaid, S .

TETRAHEDRON LETTERS, 2000, 41 (06) :797-800

[22] (-)-Cytisine and Derivatives: Synthesis, Reactivity, and Applications [J].

Rouden, Jacques ;

Lasne, Marie-Claire ;

Blanchet, Jerome ;

Baudoux, Jerome .

CHEMICAL REVIEWS, 2014, 114 (01) :712-778

[23] Total synthesis of the lupin alkaloid cytisine: comparison of synthetic strategies and routes [J].

Stead, Darren ;

O'Brien, Peter .

TETRAHEDRON, 2007, 63 (09) :1885-1896

[24] A combinatorial synthesis of a macrosphelide library utilizing a palladium-catalyzed carbonylation on a polymer support [J].

Takahashi, T ;

Kusaka, S ;

Doi, T ;

Sunazuka, T ;

Omura, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (42) :5230-5234

[25] Evans Enolates: Solution Structures of Lithiated Oxazolidinone-Derived Enolates [J].

Tallmadge, Evan H. ;

Collum, David B. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (40) :13087-13095

[26] Enantioselective Total Synthesis of (-)- and (+)-Petrosin [J].

Toya, Hiroki ;

Okano, Kentaro ;

Takasu, Kiyosei ;

Ihara, Masataka ;

Takahashi, Atsushi ;

Tanaka, Haruo ;

Tokuyama, Hidetoshi .

ORGANIC LETTERS, 2010, 12 (22) :5196-5199

[27] THE SYNTHESIS OF DL-CYTISINE [J].

VANTAMELEN, EE ;

BARAN, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (18) :4944-4945

[28] TOTAL SYNTHESIS OF OXYGENATED LUPIN ALKALOIDS [J].

VANTAMELEN, EE ;

BARAN, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (17) :4659-4670

[29] THE STEREOCHEMISTRY OF THE KETONIZATION REACTION OF ENOLS [J].

ZIMMERMAN, HE .

JOURNAL OF ORGANIC CHEMISTRY, 1955, 20 (05) :549-557

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