A Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Route to the Carbazole Natural Products 3-Methyl-9H-carbazole, Glycoborine, Glycozoline, Clauszoline K, Mukonine, and Karapinchamine A

2017 ◽  
Vol 82 (8) ◽  
pp. 4148-4159 ◽  
Author(s):  
Qiao Yan ◽  
Emma Gin ◽  
Malgorzata Wasinska-Kalwa ◽  
Martin G. Banwell ◽  
Paul D. Carr
Keyword(s):  
Natural Products ◽  
Cross Coupling ◽  
Reductive Cyclization ◽  
Palladium Catalyzed

Formal Total Syntheses of Crocacin A-D

2005 ◽  
Vol 70 (10) ◽  
pp. 1696-1708 ◽  
Author(s):  
Magnus Besev ◽  
Christof Brehm ◽  
Alois Fürstner
Keyword(s):  
Natural Products ◽  
Aldol Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Total Syntheses ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
The Common ◽  
Selective Addition

A concise route to the common polyketide fragment5of crocacin A-D (1-4) is presented which has previously been converted into all members of this fungicidal and cytotoxic family of dipeptidic natural products by various means. Our synthesis features asyn-selective titanium aldol reaction controlled by a valinol-derived auxiliary, a zinc-mediated, palladium-catalyzedanti-selective addition of propargyl mesylate10to the chiral aldehyde9, as well as a comparison of palladium-catalyzed Stille and Suzuki cross-coupling reactions for the formation of the diene moiety of the target.

Chemoselective reactions: Toward the synthesis of biologically active natural products with anticancer activities

2008 ◽  
Vol 80 (8) ◽  
pp. 1683-1691 ◽  
Author(s):  
Sébastien Reymond ◽  
Laurent Ferrié ◽  
Amandine Guérinot ◽  
Patrice Capdevielle ◽  
Janine Cossy
Keyword(s):  
Natural Products ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Biologically Active ◽  
Synthetic Approach ◽  
Anticancer Activities ◽  
Leucascandrolide A ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Active Natural

Leucascandrolide A and migrastatin were synthesized efficiently by using chemoselective reactions such as olefin metatheses. The use of an iron-catalyzed cross-coupling reaction overcame difficulties encountered with palladium-catalyzed processes in our synthetic approach toward spirangien A.

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