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

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: 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

Asymmetric Synthesis of 2,3,6-Trisubstituted Piperidines via Baylis–Hillman Adducts and Lithium Amide through Domino Reaction

Synlett ◽  
2019 ◽  
Vol 31 (06) ◽  
pp. 600-604 ◽  
Author(s):  
Mateo M. Salgado ◽  
Alejandro Manchado ◽  
Carlos T. Nieto ◽  
David Díez ◽  
Narciso M. Garrido
Keyword(s):  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Claisen Rearrangement ◽  
Domino Reaction ◽  
Amino Acid Derivative ◽  
Side Chain ◽  
Lithium Amide ◽  
Stereochemical Control ◽  
Asymmetric Michael Addition ◽  
Polysubstituted Piperidines

A convenient asymmetric synthesis of methyl (2S,3S,6R)-6-(4-fluorophenyl)-2-(4-hydroxyphenyl)-piperidine-3-carboxylate is described, starting from Baylis–Hillman adducts. The route involves a domino process: allylic acetate rearrangement, stereoselective Ireland–Claisen rearrangement and asymmetric Michael addition, which provides a δ-amino acid derivative with full stereochemical control. A subsequent chemoselective transformation of one of the side-chain groups allows an effective cyclization leading to biologically interesting polysubstituted piperidines in which the 2,6-aryl groups could be attached sequentially.

Determination of the Relative and Absolute Configuration of the Dimethylmyristoyl Side Chain of Pneumocandin B0by Asymmetric Synthesis

2002 ◽  
Vol 4 (24) ◽  
pp. 4201-4204 ◽  
Author(s):  
William R. Leonard, ◽  
Kevin M. Belyk ◽  
Dean R. Bender ◽  
David A. Conlon ◽  
David L. Hughes ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Absolute Configuration ◽  
Side Chain

Asymmetric Synthesis of Enantiomerically Enriched a-Amino Acids Containing 2-Furyl- and 2-Thienyl-1,2,4-triazoles in the Side-Chain

2014 ◽  
Vol 69 (4) ◽  
pp. 451-460 ◽  
Author(s):  
Ashot S. Saghyan ◽  
Hayarpi M. Simonyan ◽  
Satenik G. Petrosyan ◽  
Anna F. Mkrtchyan ◽  
Lilit V. Khachatryan ◽  
...  
Keyword(s):  
Amino Acids ◽  
Schiff Base ◽  
Asymmetric Synthesis ◽  
Efficient Method ◽  
Enantiomeric Excess ◽  
Side Chain ◽  
Chiral Auxiliaries ◽  
Enantiomerically Pure ◽  
Dehydroamino Acids ◽  
Hydrolysis Of

An efficient method for the asymmetric synthesis of a-amino acids, containing furyl- and thiophenyl-substituted triazoles in their side-chain, is reported. The strategy relies on Michael addition of 3,4,5-substituted 1,2,4-triazoles to the C=C bond of chiral NiII complexes containing the Schiff base formed from dehydroamino acids (dehydroalanine and (E + Z)-dehydroaminobutyric acid) and from chiral auxiliaries, i. e. (S)-2-N-(N0-benzylprolyl)aminobenzophenone and (S)-2-N- (N0-2-chlorobenzylprolyl) aminobenzophenone. The reactions proceeded with good to very good diastereoselectivity. Hydrolysis of the diastereomeric mixtures of metal complexes afforded the enantiomerically pure a-amino acids with high enantiomeric excess (ee> 98%).

Isoxazolinium Salts in Asymmetric Synthesis. 1. Stereoselective Reduction Induced by a 3’-Alkoxy Stereocentre. A New Approach to Polyfunctionalized β-Amino Acids* [1, 2]

2004 ◽  
Vol 59 (4) ◽  
pp. 451-467 ◽  
Author(s):  
Marco Henneböhle ◽  
Pierre-Yves Le Roy ◽  
Matthias Hein ◽  
Rudolf Ehrler ◽  
Volker Jäger
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Catalytic Hydrogenation ◽  
Optically Active ◽  
Side Chain ◽  
Reduction Step ◽  
One Pot ◽  
New Approach ◽  
Stereoselective Reduction

AbstractA new approach to optically active N-methylamino acids is presented, relying on stereoselective reduction of N-methylisoxazolinium salts with a dioxyethyl side-chain. The diastereoselectivity of the reduction step is studied systematically, in comparison with that of respective isoxazolines. A two-step transformation of isoxazolinium salts - with NaBH3(OAc) and subsequent catalytic hydrogenation as well as a one-pot reduction by catalytic hydrogenation led to high (95:5 and 87:13) diastereomeric ratios of protected erythro-N-methylaminopentanetriols. The hydroxyethyl side-chain is elaborated by oxidation to afford the β -N-methylamino acid 37, exemplifying the potential of this strategy.

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