Concise Total Synthesis of Dihydrocorynanthenol, Protoemetinol, Protoemetine, 3-epi-Protoemetinol and Emetine

被引：41

作者：

Lin, Shuangzheng ^{[1
,2
]}

Deiana, Luca ^{[1
,2
]}

Tseggai, Abrehet ^{[1
,2
]}

Cordova, Armando ^{[1
,2
,3
]}

机构：

[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden

[2] Stockholm Univ, Berzelii Ctr EXSELENT, S-10691 Stockholm, Sweden

[3] Mid Sweden Univ, Dept Nat Sci Engn & Math, S-85170 Sundsvall, Sweden

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 02期

关键词：

Organocatalysis; Asymmetric catalysis; Multicomponent reactions; Total synthesis; Natural products; Alkaloids; ENANTIOSPECIFIC TOTAL-SYNTHESIS; ENANTIOSELECTIVE TOTAL SYNTHESES; PICTET-SPENGLER REACTION; INDOLE ALKALOIDS; FORMAL SYNTHESIS; ASYMMETRIC-SYNTHESIS; GENERAL-APPROACH; CONJUGATE ADDITION; DIMETHYL-SULFOXIDE; ALPHA PRODUCTION;

D O I：

10.1002/ejoc.201101296

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise asymmetric assembly of secologanine tryptamine and dopamine alkaloids by means of a one-pot three-component cascade reaction methodology is disclosed. This is demonstrated by the expeditious total syntheses of (-)-dihydrocorynanthenol, (-)-protoemetinol, (-)-protoemetine, (-)-3-epi-protoemetinol, and emetine (3-6 steps). The biomimetic synthetic strategy involved the following key steps: (i) One-pot three-component highly enantioselective catalytic Michael/Pictet-Spengler/lactamization cascade reactions; (ii) One-pot tandem Swern oxidation/Wittig sequences; (iii) One-pot tandem hydrogenation sequences.

引用

页码：398 / 408

页数：11

共 117 条

[71] Concise syntheses of (±)-protoemetinol and related alkaloids using radical cyclisation
Palframan, Matthew J.
Parsons, Andrew F.
Johnson, Paul
[J]. TETRAHEDRON LETTERS, 2011, 52 (11) : 1154 - 1156
[72] Anti-inflammatory activity of aucubin by inhibition of tumor necrosis factor-α production in RAW 264.7 cells
Park, KS
Chang, IM
[J]. PLANTA MEDICA, 2004, 70 (08) : 778 - 779
[73] Paul B. H., 1894, JAHRESBER PHARM, P523
[74] Asymmetric domino reactions. Part B: Reactions based on the use of chiral catalysts and biocatalysts
Pelissier, H
[J]. TETRAHEDRON, 2006, 62 (10) : 2143 - 2173
[75] Pelletier P.-J., 1817, JOUR D, P145
[76] Pilling A.W., 2007, Angew. Chem, V119, P5524
[77] Site-isolated base- and acid-mediated Michael-initiated cyclization cascades
Pilling, Adam W.
Boehmer, Jutta
Dixon, Darren J.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (28) : 5428 - 5430
[78] Enantioselective pictet-spengler-type cyclizations of hydroxylactams: H-bond donor catalysis by anion binding
Raheem, Izzat T.
Thiara, Parvinder S.
Peterson, Emily A.
Jacobsen, Eric N.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (44) : 13404 - +
[79] Ramon D.J., 2005, ANGEW CHEM INT EDIT, V117, P1628, DOI DOI 10.1002/ANGE.200460548
[80] Asymmetric multicomponent reactions (AMCRs):: The new frontier
Ramón, DJ
Yus, M
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (11) : 1602 - 1634

← 3 4 5 6 7 8 9 10 11 12 →