scholarly journals Asymmetric Synthesis of Chiral 1,3-Dimethyl Units Through a Double Michael Reaction of Nitromethane and Crotonaldehyde Catalyzed by Diphenylprolinol Silyl Ether

Synlett ◽  
2019 ◽  
Vol 30 (04) ◽  
pp. 442-448
Author(s):  
Yujiro Hayashi ◽  
Shunsuke Toda
Keyword(s):  
Asymmetric Synthesis ◽  
Present Method ◽  
Michael Reaction ◽  
Side Chain ◽  
Silyl Ether ◽  
Synthetic Route

An efficient synthetic route to install chiral 1,3-dimethyl units through a double Michael reaction of crotonaldehyde and nitromethane catalyzed by diphenylprolinol silyl ether is developed. Either 1,3-syn- or 1,3-anti-dimethyl units are obtained selectively depending on the enantiomer of the diphenylprolinol silyl ether catalyst used. The side chain of pneumocandin B0 is synthesized enantioselectively by using the present method as a key step.

Asymmetric Synthesis of Pentasubstituted Cyclohexanes through Diphenylprolinol Silyl Ether Mediated Domino Michael/Michael Reaction

2021 ◽  
Author(s):  
Amaechi Shedrack Odoh ◽  
Louise Aidanpää ◽  
Nariyoshi Umekubo ◽  
Hiroaki Matoba ◽  
Naoki Mori ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Reaction ◽  
Silyl Ether

scholarly journals Investigation of the Anti-Methicillin-Resistant Staphylococcus aureus Activity of (+)-Tanikolide- and (+)-Malyngolide-Based Analogues Prepared by Asymmetric Synthesis

2021 ◽  
Vol 22 (12) ◽  
pp. 6400
Author(s):  
Joseph Breheny ◽  
Cian Kingston ◽  
Robert Doran ◽  
Joao Anes ◽  
Marta Martins ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Asymmetric Synthesis ◽  
Methicillin Resistant Staphylococcus Aureus ◽  
Antimicrobial Properties ◽  
Side Chain ◽  
Alkyl Side Chain ◽  
Methicillin Resistant ◽  
Antibacterial And Antifungal

Herein, we report antibacterial and antifungal evaluation of a series of previously prepared (+)-tanikolide analogues. One analogue, (4S,6S)-4-methyltanikolide, displayed promising anti-methicillin-resistant Staphylococcus aureus activity with a MIC of 12.5 µg/mL. Based on the antimicrobial properties of the structurally related (−)-malyngolide, two further analogues (4S,6S)-4-methylmalyngolide and (4R,6S)-4-methylmalyngolide bearing a shortened n-nonyl alkyl side chain were prepared in the present study using a ZrCl4-catalysed deprotection/cyclisation as the key step in their asymmetric synthesis. When these were tested for activity against anti-methicillin-resistant Staphylococcus aureus, the MIC increased to 50 µg/mL.

ChemInform Abstract: Base-Dependent Stereodivergent Intramolecular Aza-Michael Reaction: Asymmetric Synthesis of 1,3-Disubstituted Isoindolines.

ChemInform ◽  
2014 ◽  
Vol 45 (3) ◽  
pp. no-no
Author(s):  
Santos Fustero ◽  
Lidia Herrera ◽  
Ruben Lazaro ◽  
Elsa Rodriguez ◽  
Miguel A. Maestro ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Reaction

Concise Synthesis of the Terpene Core Structure of Suaveolindole Through a Time-Economic Route

Synlett ◽  
2021 ◽  
Author(s):  
Hiroki Tanimoto ◽  
Kazuki Tojo ◽  
Tsumoru Morimoto ◽  
Kiyomi Kakiuchi
Keyword(s):  
Claisen Rearrangement ◽  
Core Structure ◽  
Side Chain ◽  
Unsaturated Ester ◽  
Synthetic Route ◽  
Carbon Side Chain

The terpene core structure of suaveolindoles was synthesized through a concise route in a time-economical manner. A scalable synthetic route from pulegone delivered the desired α,β,γ,δ-unsaturated ester in a brief period. By way of Eschenmoser-Claisen rearrangement, carbon side chain moiety at the crowded double-allylic position was introduced stereoselectively.

Asymmetric Synthesis of the Chlorocyclopropane-Containing Callipeltoside A Side Chain

2001 ◽  
Vol 3 (4) ◽  
pp. 503-505 ◽  
Author(s):  
David A. Evans ◽  
Jason D. Burch
Keyword(s):  
Asymmetric Synthesis ◽  
Side Chain ◽  
Callipeltoside A

ChemInform Abstract: An Efficient Asymmetric Synthesis of the Mercaptopyrrolidine Side Chain of an Important β-Methyl Carbapenem Antibiotic.

ChemInform ◽  
2010 ◽  
Vol 28 (33) ◽  
pp. no-no
Author(s):  
J. D. III ARMSTRONG ◽  
J. L. KELLER ◽  
J. LYNCH ◽  
T. LIU ◽  
F. W. JUN. HARTNER ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Side Chain ◽  
Carbapenem Antibiotic

scholarly journals Catalytic asymmetric formal synthesis of beraprost

2015 ◽  
Vol 11 ◽  
pp. 2654-2660 ◽  
Author(s):  
Yusuke Kobayashi ◽  
Ryuta Kuramoto ◽  
Yoshiji Takemoto
Keyword(s):  
Asymmetric Synthesis ◽  
Michael Reaction ◽  
Subsequent Reduction ◽  
Formal Synthesis ◽  
Michael Adduct ◽  
Catalytic Asymmetric Synthesis ◽  
Weinreb Amide ◽  
Tricyclic Core ◽  
Catalytic Asymmetric

The first catalytic asymmetric synthesis of the key intermediate for beraprost has been achieved through an enantioselective intramolecular oxa-Michael reaction of an α,β-unsaturated amide mediated by a newly developed benzothiadiazine catalyst. The Weinreb amide moiety and bromo substituent of the Michael adduct were utilized for the C–C bond formations to construct the scaffold. All four contiguous stereocenters of the tricyclic core were controlled via Rh-catalyzed stereoselective C–H insertion and the subsequent reduction from the convex face.

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