scholarly journals Stereoselective Synthesis of Selenium-Containing Glycoconjugates via the Mitsunobu Reaction

Molecules ◽  
2021 ◽  
Vol 26 (9) ◽  
pp. 2541
Author(s):  
Luigia Serpico ◽  
Mauro De Nisco ◽  
Flavio Cermola ◽  
Michele Manfra ◽  
Silvana Pedatella
Keyword(s):  
Stereoselective Synthesis ◽  
Antioxidant Properties ◽  
Mitsunobu Reaction ◽  
Efficient Route ◽  
Target Molecules

A simple and efficient route for the synthesis of new glycoconjugates has been developed. The approach acts as a model for a mini-library of compounds with a deoxy-selenosugar core joined to a polyphenolic moiety with well-known antioxidant properties. An unexpected stereocontrol detected in the Mitsunobu key reaction led to the most attractive product showing a natural d-configuration. Thus, we were able to obtain the target molecules from the commercially available d-ribose via a shorter and convenient sequence of reactions.

Directed Ortho-Lithiation of Aminophosphazenes: An Efficient Route to the Stereoselective Synthesis of P-Chiral Compounds

2013 ◽  
Vol 15 (10) ◽  
pp. 2378-2381 ◽  
Author(s):  
María Casimiro ◽  
Laura Roces ◽  
Santiago García-Granda ◽  
María José Iglesias ◽  
Fernando López Ortiz
Keyword(s):  
Stereoselective Synthesis ◽  
Chiral Compounds ◽  
Efficient Route

Formation of heterocycles by the Mitsunobu reaction. Stereoselective synthesis of (+)-α-skytanthine

1996 ◽  
Vol 37 (14) ◽  
pp. 2463-2466 ◽  
Author(s):  
Tetsuto Tsunoda ◽  
Fumie Ozaki ◽  
Nozomi Shirakata ◽  
Yuki Tamaoka ◽  
Hidetoshi Yamamoto ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Mitsunobu Reaction

Expeditious Stereoselective Synthesis of l-Iminosugar Precursors via a Mitsunobu Reaction

Synlett ◽  
2009 ◽  
Vol 2009 (06) ◽  
pp. 978-980
Author(s):  
Véronique Barragan-Montero ◽  
Jean-Louis Montero ◽  
Antoine Bussière ◽  
Khalid Oumzil ◽  
Jean-Yves Winum
Keyword(s):  
Stereoselective Synthesis ◽  
Mitsunobu Reaction

Stereoselective synthesis of naturally occurring unsaturated amide alkaloids by a modified Ramberg–Bäcklund reaction

2004 ◽  
Vol 82 (5) ◽  
pp. 622-630 ◽  
Author(s):  
Yang Li ◽  
Yu Zhang ◽  
Zhi Huang ◽  
Xiaoping Cao ◽  
Kun Gao
Keyword(s):  
Potassium Hydroxide ◽  
Stereoselective Synthesis ◽  
Starting Material ◽  
Mitsunobu Reaction ◽  
Dichloromethane Solution ◽  
Naturally Occurring

A convenient and rapid approach for the synthesis of naturally occurring unsaturated amide alkaloids 1a–1n by the recently developed one-flask Ramberg–Bäcklund reaction is described. The starting material was alcohol 3, which was transformed into thiolacetate 4 using the Mitsunobu reaction. In situ cleavage of acetyl moiety of 4, followed by alkylation of the resulting thiol with appropriate chloroacetamide 5, provided the sulfide 6. Oxidation of sulfide 6 gave the corresponding sulfone 2. Treatment of the sulfone 2 with the dibromodifluoromethane in the presence of alumina-supported potassium hydroxide in dichloromethane solution afforded unsaturated amide alkaloids 1a–1n. To the best of our knowledge, the synthesis of 1e and 1i was reported for the first time.Key words: synthesis, unsaturated amide alkaloids, Ramberg–Bäcklund reaction.

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