Five-Step Total Synthesis of (±)-Aspidospermidine by a Lactam Strategy via an Azomethine Ylide

2021 ◽  
Vol 23 (8) ◽  
pp. 3058-3063
Author(s):  
Seiya Katahara ◽  
Yasukazu Sugiyama ◽  
Mina Yamane ◽  
Yukinori Komiya ◽  
Takaaki Sato ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Azomethine Ylide

Total Synthesis of Proposed Structure of Yuremamine and All Diastereomers Using [3+2]-Cycloaddition of Platinum-Containing Azomethine Ylide

2015 ◽  
Vol 10 (9) ◽  
pp. 1850-1853 ◽  
Author(s):  
Tomoya Ohyama ◽  
Masako Uchida ◽  
Hiroyuki Kusama ◽  
Nobuharu Iwasawa
Keyword(s):  
Total Synthesis ◽  
Azomethine Ylide

Stereoselective construction of 5,11-methanomorphanthridine and 5,10b-phenanthridine structural frameworks: Total syntheses of (±)-pancracine, (±)-brunsvigine, (±)-maritidine, and (±)-crinine

2012 ◽  
Vol 84 (7) ◽  
pp. 1597-1619 ◽  
Author(s):  
Ganesh Pandey ◽  
Smita R. Gadre
Keyword(s):  
Total Synthesis ◽  
Core Structure ◽  
Biologically Active ◽  
Single Electron ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Total Syntheses ◽  
The Core ◽  
One Step

The core structure of the complex pentacyclic 5,11-methanomorphanthridine skeleton and the vicinal quaternary and tertiary stereocenters of the 5,10b-phenanthridine skeleton are constructed stereospecifically in one step employing intramolecular 1,3-dipolar cycloaddition of a nonstabilized azomethine ylide (AMY) generated by the sequential double desilylation of appropriate bis-trimethylsilylmethyl amines using Ag(I)F as a single-electron oxidant. The strategy is successfully applied for the total synthesis of biologically active alkaloids such as (±)-pancracine, (±)-brunsvigine, (±)-maritidine, and (±)-crinine.

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