An improved synthesis of sitophilure

2009 ◽  
Vol 87 (1) ◽  
pp. 30-32 ◽  
Author(s):  
Cuifen Lu ◽  
Junqi Nie ◽  
Guichun Yang ◽  
Zuxing Chen
Keyword(s):  
Asymmetric Synthesis ◽  
Aldol Reaction ◽  
Enantiomeric Excess ◽  
Chiral Auxiliary

The asymmetric synthesis of sitophilure was carried out in 8 steps, with 42% overall yield and 97% enantiomeric excess from propionaldehyde. The synthesis relied on an approach employing an asymmetric acyl-thiazolidinethione propionate aldol reaction to establish two stereogenic centers.Key words: sitophilure, thiazolidinethione, chiral auxiliary, synthesis.

Indium Bromide-catalyzed Unprecedented Hydrogenolysis: A Novel One-Pot Synthesis of Per-O-Acetylated β-carboxymethyl O and S-glycosides

2020 ◽  
Vol 24 (8) ◽  
pp. 900-908
Author(s):  
Ram Naresh Yadav ◽  
Amrendra K Singh ◽  
Bimal Banik
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Auxiliary ◽  
Bioactive Molecules ◽  
One Pot ◽  
Enantiomerically Pure ◽  
Stereoselective Glycosylation ◽  
One Pot Synthesis ◽  
Wide Range

Numerous O (oxa)- and S (thia)-glycosyl esters and their analogous glycosyl acids have been accomplished through stereoselective glycosylation of various peracetylated bromo sugar with benzyl glycolate using InBr3 as a glycosyl promotor followed by in situ hydrogenolysis of resulting glycosyl ester. A tandem glycosylating and hydrogenolytic activity of InBr3 has been successfully investigated in a one-pot procedure. The resulting synthetically valuable and virtually unexplored class of β-CMGL (glycosyl acids) could serve as an excellent potential chiral auxiliary in the asymmetric synthesis of a wide range of enantiomerically pure medicinally prevalent β-lactams and other bioactive molecules of diverse medicinal interest.

Asymmetric Synthesis of Iridoid Derivatives Using Resolved 2-Phenylindoline as a Chiral Auxiliary

2008 ◽  
Vol 2008 (35) ◽  
pp. 5915-5921 ◽  
Author(s):  
Ellen M. Santangelo ◽  
Ilme Liblikas ◽  
Anoma Mudalige ◽  
Karl W. Törnroos ◽  
Per-Ola Norrby ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Auxiliary
Sign in / Sign up

Export Citation Format

Share Document