Efficient and practical asymmetric synthesis of the taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenylisoserine, and its analogs via chiral 3-hydroxy-4-aryl-.beta.-lactams through chiral ester enolate-imine cyclocondensation

1991 ◽  
Vol 56 (5) ◽  
pp. 1681-1683 ◽  
Author(s):  
Iwao Ojima ◽  
Ivan Habus ◽  
Mangzhu Zhao ◽  
Gunda I. Georg ◽  
Lalith R. Jayasinghe
Keyword(s):  
Asymmetric Synthesis ◽  
Side Chain ◽  
Beta Lactams ◽  
Ester Enolate

scholarly journals Asymmetric Synthesis of .beta.-Lactams via the Zinc-Mediated Glycine Ester Enolate-Imine Condensation Reaction Using .alpha.-Amino Esters as the Chiral Auxiliary

1995 ◽  
Vol 60 (14) ◽  
pp. 4331-4338 ◽  
Author(s):  
Hendrik L. van Maanen ◽  
Henk Kleijn ◽  
Johann T. B. H. Jastrzebski ◽  
Jan Verweij ◽  
Antonius P. G. Kieboom ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Condensation Reaction ◽  
Chiral Auxiliary ◽  
Beta Lactams ◽  
Amino Esters ◽  
Ester Enolate

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.

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

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.

Efficient Asymmetric Synthesis of cis-4-Formyl .beta.-Lactams from L-(+)-Tartaric Acid

1994 ◽  
Vol 59 (4) ◽  
pp. 932-934 ◽  
Author(s):  
M. Jayaraman ◽  
A. R. A. S. Deshmukh ◽  
B. M. Bhawal
Keyword(s):  
Asymmetric Synthesis ◽  
Tartaric Acid ◽  
Beta Lactams

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
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