Studies Toward an Asymmetric Synthesis of CP-263,114 and CP-225,917

2000 ◽  
Vol 65 (4) ◽  
pp. 490-510 ◽  
Author(s):  
Jean-François Devaux ◽  
Steven V. O'Neil ◽  
Nathalie Guillo ◽  
Leo A. Paquette
Keyword(s):  
Benzoic Acid ◽  
Asymmetric Synthesis ◽  
Claisen Rearrangement ◽  
Metal Reduction ◽  
Birch Reduction ◽  
Highly Efficient ◽  
Stereogenic Centers

An enantioselective approach to construction of the complex framework of the CP compounds is presented. The synthesis relies on initial elaboration of the two sidechains. The "upper" appendage was asymmetrically dihydroxylated with both AD-mix reagents in order to lend flexibility to the scheme and provide the necessary handle for evolving the additional stereogenic centers. These fragments were linked to benzoic acid via Birch reduction-alkylation and subsequent cuprate addition. A series of functionalization reactions including dissolving metal reduction, Claisen rearrangement, iodolactonization, regioselective epoxide cleavage-oxidation, and intramolecular Wadsworth-Emmons cyclization took advantage of highly efficient stereocontrol. However, this flexibility was thwarted when deprotonation of a penultimate intermediate failed to be regioselective in the proper direction.

Convergent Asymmetric Synthesis of a Renin Inhibitor: A Highly Efficient Construction Method of Three Stereogenic Centers

2013 ◽  
Vol 17 (11) ◽  
pp. 1430-1439 ◽  
Author(s):  
Makoto Michida ◽  
Yoshihiro Takayanagi ◽  
Makoto Imai ◽  
Yukito Furuya ◽  
Kenichi Kimura ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Construction Method ◽  
Renin Inhibitor ◽  
Highly Efficient ◽  
Stereogenic Centers ◽  
Efficient Construction

Synthetic Studies toward Tubiferal A: Asymmetric Synthesis of a Model ABC-ring Compound

Synlett ◽  
2021 ◽  
Author(s):  
Yuki Yukutake ◽  
Takahiro Hiramatsu ◽  
Ryusei Itoh ◽  
Kazutada Ikeuchi ◽  
Takahiro Suzuki ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Claisen Rearrangement ◽  
Ring System ◽  
Alkylation Reaction ◽  
Ring Model ◽  
Stereoselective Addition ◽  
Stereogenic Centers ◽  
Rearrangement Reaction ◽  
Synthetic Studies ◽  
Ab Ring

Synthetic studies on an ABC-ring model of Tubiferal A, a triterpenoid isolated from the fruit bodies of the Tubifera dimorphotheca myxomycete, are described. The stereogenic centers at the angular positions were constructed through the stereoselective addition of a C-ring allylborane followed by an Eschenmoser–Claisen rearrangement reaction prior to the formation of the AB-ring system by a double intramolecular alkylation reaction of a dichloro nitrile intermediate.

scholarly journals Advances on Greener Asymmetric Synthesis of Antiviral Drugs via Organocatalysis

2021 ◽  
Vol 14 (11) ◽  
pp. 1125
Author(s):  
Everton M. da Silva ◽  
Hérika D. A. Vidal ◽  
Arlene G. Corrêa
Keyword(s):  
Pharmaceutical Industry ◽  
Antiviral Activity ◽  
Asymmetric Synthesis ◽  
High Mortality ◽  
Viral Infections ◽  
Mortality Rates ◽  
Chiral Drugs ◽  
Stereogenic Centers ◽  
Synthetic Routes ◽  
New Compounds

Viral infections cause many severe human diseases, being responsible for remarkably high mortality rates. In this sense, both the academy and the pharmaceutical industry are continuously searching for new compounds with antiviral activity, and in addition, face the challenge of developing greener and more efficient methods to synthesize these compounds. This becomes even more important with drugs possessing stereogenic centers as highly enantioselective processes are required. In this minireview, the advances achieved to improve synthetic routes efficiency and sustainability of important commercially antiviral chiral drugs are discussed, highlighting the use of organocatalytic methods.

scholarly journals Advances on Greener Asymmetric Synthesis of Antiviral Drugs via Organocatalysis

2021 ◽  
Author(s):  
Arlene Gonçalves Corrêa ◽  
Everton Machado da Silva ◽  
Herika Danielle Almeida Vidal
Keyword(s):  
Pharmaceutical Industry ◽  
Antiviral Activity ◽  
Asymmetric Synthesis ◽  
High Mortality ◽  
Viral Infections ◽  
Mortality Rates ◽  
Chiral Drugs ◽  
Stereogenic Centers ◽  
Synthetic Routes ◽  
New Compounds

Viral infections inflict many serious human diseases, being responsible for remarkably high mortality rates. In this sense, both the academy and the pharmaceutical industry are continuously searching for new compounds with antiviral activity, and in addition, face the challenge of developing greener and more efficient methods to synthesize these compounds. This becomes even more important with drugs possessing stereogenic centers as highly enantioselective processes are required. In this minireview, the advances achieved to improve synthetic routes efficiency and sustainability of important commercially antiviral chiral drugs are discussed, highlighting the use of organocatalytic methods.

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