AgOTf/I2-Mediated Cyclization/Cross-Coupling/Isomerization of Enynones with Phosphorus Ylides: An Expedient Route to Stereoselective Synthesis of (E)-2-Alkenylfurans

2021 ◽  
Author(s):  
Ling Tang ◽  
Yangyi Zhang ◽  
Guisheng Deng
Keyword(s):  
Stereoselective Synthesis ◽  
Cross Coupling ◽  
Phosphorus Ylides

scholarly journals Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment

2020 ◽  
Vol 16 ◽  
pp. 670-673
Author(s):  
Jan Geldsetzer ◽  
Markus Kalesse
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Cross Coupling ◽  
Vinyl Bromide ◽  
Type Coupling ◽  
Chiral Centers

The stereoselective synthesis of the (Z)-enamide fragment of chondrochloren (1) is described. A Buchwald-type coupling between amide 3 and (Z)-bromide 4 was used to generate the required fragment. The employed amide 3 comprising three chiral centers was obtained through a seven-step sequence starting from ᴅ-ribonic acid-1,4-lactone. The (Z)-vinyl bromide 4 is accessible in four steps from 4-hydroxybenzaldehyde. The pivotal cross coupling between both fragments was achieved after extensive experimentation with copper(I) iodide, K2CO3 and N,N′-dimethylethane-1,2-diamine.

ChemInform Abstract: Highly Stereoselective Synthesis of 2-Methyl-1,3-dienes by Palladium-Catalyzed Cross-Coupling Reaction with Trimethylaluminum.

ChemInform ◽  
2014 ◽  
Vol 45 (33) ◽  
pp. no-no
Author(s):  
Masahiro Miyazawa ◽  
Risa Takehana ◽  
Takao Sanga ◽  
Aoi Hosomori ◽  
Hajime Yokoyama ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed
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