Tandem Nucleophilic Addition/Oxy-2-azonia-Cope Rearrangement for the Formation of Homoallylic Amides and Lactams: Total Synthesis and Structural Verification of Motuporamine G

2012 ◽  
Vol 134 (49) ◽  
pp. 20009-20012 ◽  
Author(s):  
Lijun Zhou ◽  
Zhiming Li ◽  
Yue Zou ◽  
Quanrui Wang ◽  
Italo A. Sanhueza ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Nucleophilic Addition ◽  
Cope Rearrangement

Total Synthesis of (–)-Alstofolinine A: Selected Furan Oxidation/ Cyclization Cascade

Synlett ◽  
2019 ◽  
Vol 31 (01) ◽  
pp. 7-12 ◽  
Author(s):  
Ye Zhang ◽  
Lei Zhang ◽  
Xiangbing Qi
Keyword(s):  
Total Synthesis ◽  
Common Core ◽  
Nucleophilic Addition ◽  
Addition Reaction ◽  
Indole Alkaloids ◽  
Indole Alkaloid ◽  
Asymmetric Total Synthesis ◽  
Ring Systems ◽  
Synthetic Strategy ◽  
Nucleophilic Addition Reaction

Indole-fused tetracyclic ring systems containing nitrogen atoms are common core skeletons of many indole alkaloids such as sarpagine, macroline, and ajmaline. Efficient and stereoselective construction of these ring systems can promote the development of the corresponding alkaloid syntheses. In this article, we briefly summarize our current progress toward the application of the aza-Achmatowicz reaction and indole nucleophilic addition reaction cascade for the first asymmetric total synthesis of the macroline-type indole alkaloid (–)-Alstofolinine A. Our synthetic strategy is based on furan oxidation/rearrangement and proceeds from easily accessible materials such as indole and furan derivatives.

scholarly journals Aza-Cope Rearrangement−Mannich Cyclizations for the Formation of Complex Tricyclic Amines:  Stereocontrolled Total Synthesis of (±)-Gelsemine

2005 ◽  
Vol 127 (51) ◽  
pp. 18046-18053 ◽  
Author(s):  
William G. Earley ◽  
Jon E. Jacobsen ◽  
Andrew Madin ◽  
G. Patrick Meier ◽  
Christopher J. O'Donnell ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Cope Rearrangement

scholarly journals Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps

2018 ◽  
Vol 16 (5) ◽  
pp. 750-755 ◽  
Author(s):  
Pratap R. Jagtap ◽  
Ivana Císařová ◽  
Ullrich Jahn
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Nucleophilic Addition ◽  
Key Steps ◽  
Redox Isomerization

Three steps suffice to complete a bioinspired total synthesis of tetrahydrofuran lignans using tandem addition/isomerization/dimerization and cycloetherification reactions.

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