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
收藏
页码：398 / 408
页数：11
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