Total Synthesis of (+)-Mesembrine Applying Asymmetric Gold Catalysis

被引：36

作者：

Spittler, Michael ^{[1
]}

Lutsenko, Kiril ^{[1
]}

Czekelius, Constantin ^{[1
]}

机构：

[1] Univ Dusseldorf, Inst Organ Chem & Macromol Chem, Univ Str 1, D-40225 Dusseldorf, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 14期

关键词：

QUATERNARY CARBON CENTERS; FORMAL TOTAL-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; SCELETIUM ALKALOIDS; CONCISE SYNTHESIS; EFFICIENT; (-)-MESEMBRINE; CONSTRUCTION; SULFONAMIDES; KETONES;

D O I：

10.1021/acs.joc.6b00985

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of enantiomerically pure (+)-mesembrine is described. The central pyrrolidine moiety incorporating a quaternary, all-carbon-substituted stereocenter was constructed employing an asymmetric gold-catalyzed cydoisomerization of a 1,4-diynamide.

引用

页码：6100 / 6105

页数：6

共 65 条

[1] Alternative synthetic methods through new developments in catalysis by gold [J].

Arcadi, Antonio .

CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325

[2] Gold-catalyzed decorations of arenes and heteroarenes with C-C multiple bonds [J].

Bandini, Marco .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (03) :1358-1367

[3] New route to 4-aminocyclopent-2-en-1-ols: Synthesis and enantioselective rearrangement of 4-amino-substituted cyclopentene oxides [J].

Barrett, S ;

O'Brien, P ;

Steffens, HC ;

Towers, TD ;

Voith, M .

TETRAHEDRON, 2000, 56 (49) :9633-9640

[4]

BODENDORF K., 1957, ARCH PHARM U BER DEUTSCH PHARM GES, V290, P441, DOI 10.1002/ardp.19572901002

[5]

Chemla F, 2000, SYNTHESIS-STUTTGART, P75

[6] Gold-Catalyzed Carbon-Heteroatom Bond-Forming Reactions [J].

Corma, A. ;

Leyva-Perez, A. ;

Sabater, Maria J. .

CHEMICAL REVIEWS, 2011, 111 (03) :1657-1712

[7] A concise synthesis of (-)-mesembrine [J].

Dalko, PI ;

Brun, V ;

Langlois, Y .

TETRAHEDRON LETTERS, 1998, 39 (49) :8979-8982

[8] Asymmetric construction of a quaternary carbon center by tandem [4+2]/[3+2] cycloaddition of a nitroalkene. The total synthesis of (-)-mesembrine [J].

Denmark, SE ;

Marcin, LR .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1675-1686

[9] Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity [J].

Dorel, Ruth ;

Echavarren, Antonio M. .

CHEMICAL REVIEWS, 2015, 115 (17) :9028-9072

[10] Gold and platinum catalysis-a convenient tool for generating molecular complexity [J].

Fuerstner, Alois .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3208-3221

← 1 2 3 4 5 6 7 →