ChemInform Abstract: Enantioselective Functionalization of Prochiral Diols via Chiral Spiroketals: Preparation of Optically Pure 2-Substituted 1,3-Propanediol Derivatives and Asymmetric Synthesis of Chroman Ring and Side Chain of α-Tocopherol.

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.

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Asymmetric Synthesis of the Chlorocyclopropane-Containing Callipeltoside A Side Chain

Organic Letters ◽

10.1021/ol0155182 ◽

2001 ◽

Vol 3 (4) ◽

pp. 503-505 ◽

Cited By ~ 48

Author(s):

David A. Evans ◽

Jason D. Burch

Keyword(s):

Asymmetric Synthesis ◽

Side Chain ◽

Callipeltoside A

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ChemInform Abstract: Expeditious Asymmetric Synthesis of Optically Pure δ-Lactones Bearing Consecutive Three Asymmetric Centers.

ChemInform ◽

10.1002/chin.199250076 ◽

2010 ◽

Vol 23 (50) ◽

pp. no-no

Author(s):

Y. NAGAO ◽

T. TOHJO ◽

M. OCHIAI ◽

M. SHIRO

Keyword(s):

Asymmetric Synthesis ◽

Optically Pure

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An Ultimate Stereocontrol in Asymmetric Synthesis of Optically Pure Fully Aromatic Helicenes

Journal of the American Chemical Society ◽

10.1021/jacs.5b02794 ◽

2015 ◽

Vol 137 (26) ◽

pp. 8469-8474 ◽

Cited By ~ 61

Author(s):

Michal Šámal ◽

Serghei Chercheja ◽

Jiří Rybáček ◽

Jana Vacek Chocholoušová ◽

Jaroslav Vacek ◽

...

Keyword(s):

Asymmetric Synthesis ◽

Optically Pure

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

ChemInform ◽

10.1002/chin.199733319 ◽

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

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

Synlett ◽

10.1055/s-0039-1690990 ◽

2019 ◽

Vol 31 (06) ◽

pp. 600-604 ◽

Cited By ~ 1

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.

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