Lactam Strategy Using Amide-Selective Nucleophilic Addition for the Quick Access to Complex Amines: Unified Total Synthesis of Stemoamide-Type Alkaloids

2022 ◽  
Author(s):  
Yasukazu Sugiyama ◽  
Yasuki Soda ◽  
Makoto Yoritate ◽  
Hayato Tajima ◽  
Yoshito Takahashi ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Nucleophilic Addition

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 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.

ChemInform Abstract: Total Synthesis of (.+-.)-Gephyrotoxin by Amide-Selective Reductive Nucleophilic Addition.

ChemInform ◽  
2014 ◽  
Vol 45 (30) ◽  
pp. no-no
Author(s):  
Kenji Shirokane ◽  
Takamasa Wada ◽  
Makoto Yoritate ◽  
Ryo Minamikawa ◽  
Nobuaki Takayama ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Nucleophilic Addition

How to Start a Total Synthesis from the Wieland-Miescher Ketone?

2019 ◽  
Vol 16 (3) ◽  
pp. 328-341
Author(s):  
Zai-Qun Liu
Keyword(s):  
Total Synthesis ◽  
Nucleophilic Addition ◽  
Vinyl Ketone ◽  
Methyl Vinyl Ketone ◽  
Methyl Vinyl ◽  
Oxidation Reduction ◽  
The Future ◽  
Robinson Annulation

Background: he Wieland-Miescher ketone consists of a couple of enantiomers of 9-methyl- Δ5(10)-octalin-1,6-dione, in which the configuration at 9-position is S- or R-type. The Robinson annulation of 2-methyl-1,3-cyclohexanedione with methyl vinyl ketone is able to afford the Wieland-Miescher ketone. As widely used in the total synthesis, the Wieland-Miescher ketone is treated at the beginning of total synthesis, and protocols for treating the Wieland-Miescher ketone are worthy to be addressed. Objective: The presented review provides the progress of the usage of Wieland-Miescher ketone for the total synthesis, while treatments on C=C and C=O in the Wieland-Miescher ketone at the beginning of total synthesis are exemplified herein. Conclusion: Modifications of the Wieland-Miescher ketone are composed of oxidation, reduction, and electrophilic or nucleophilic addition. In addition, protection of non-conjugated C=O with glycol or protection of conjugated C=O with ethanedithiol, and the introduction of substituents into α-position of C=C can also be used to modify the structure of the Wieland-Miescher ketone. It is reasonably believed that many novel strategies will be found to treat the Wieland-Miescher ketone in the future total synthesis.

The total synthesis of (±)-4-demethoxy-10-nordaunomycinone

1987 ◽  
Vol 65 (6) ◽  
pp. 1375-1379 ◽  
Author(s):  
C. M. Wong ◽  
P. M. Gordon ◽  
A. G. Chen ◽  
H. Y. P. Lam
Keyword(s):  
Total Synthesis ◽  
Phthalic Anhydride ◽  
Aluminum Chloride ◽  
Trifluoroacetic Acid ◽  
Nucleophilic Addition ◽  
Mercuric Acetate ◽  
Iron Pentacarbonyl ◽  
Magnesium Bromide ◽  
Acetate Oxidation ◽  
Hydride Reduction

4-Demethoxy-10-nordaunomycinone (4) is synthesized starting with 4,7-dimethoxy-1-indanone (8). Nucleophilic addition of ethynyl magnesium bromide to 8 followed by mercuric acetate oxidation and iron pentacarbonyl – tri-n-butyltin hydride reduction gave 4,7-dimethoxy-1-acetylindane (16). Condensation of 16 with phthalic anhydride followed by methylation with dimethylsulfate and oxidation gave 22, which was epimerized to 24 by 2,2-dimethoxypropane and trifluoroacetic acid. Demethylation of 24 with aluminum chloride gave the 4-demethoxy-10-nordaunomycinone (4).

Total synthesis of complex alkaloids by nucleophilic addition to amides

2018 ◽  
Vol 16 (21) ◽  
pp. 3864-3875 ◽  
Author(s):  
Takaaki Sato ◽  
Makoto Yoritate ◽  
Hayato Tajima ◽  
Noritaka Chida
Keyword(s):  
Total Synthesis ◽  
Nucleophilic Addition ◽  
Recent Progress ◽  
Nucleophilic Additions ◽  
Tertiary Amides ◽  
Secondary Amides

This mini review focuses on the recent progress of total synthesis of complex alkaloids based on the nucleophilic additions toN-alkoxyamides, tertiary amides and secondary amides.

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