Enantiodivergent syntheses of (+)- and (−)-1-(2,6-dimethylphenoxy)propan-2-ol: A way to access (+)- and (−)-mexiletine from D-(+)-mannitol

Manna, Avrajit; Chatterjee, Shankar; Chakraborty, Ipsita; Bhaumik, Tanurima

doi:10.1016/j.carres.2019.107892

Cited by 3 publications

(1 citation statement)

References 55 publications

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“…In the absence of a good crystal for X-ray analysis, the stereocenter in (+)- 34 was assigned via analogy to a previously reported alkylation of a substrate similar to (+)- 32 . In three additional steps involving (1) reductive removal of the oxazolidinone, (2) treatment of the resultant alcohol with p- toluenesulfonyl chloride, and (3) displacement of the 1° tosylate using LiAlH 4 , orthogonally protected (+)- 21 could be accessed in an acceptable overall yield (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Asymmetric Total Synthesis and Revision of Absolute Stereochemistry for (+)-Taumycin A: An Approach that Exploits Orthogonally Protected Quasienantiomers

Shrestha¹,

Golliher²,

Newar³

et al. 2021

J. Org. Chem.

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The first asymmetric total synthesis of C(9)-S-(+)-taumycin A is now reported using an approach that targeted both C(9) diastereomers concurrently. To facilitate this work, we called upon the symmetrical nature of a C(5)−C(13) side-chain intermediate and exploited orthogonal protecting groups as a tactic to access both stereoisomers from a single chiral, nonracemic intermediate. In addition to our successful approach, several minor detours that helped refine our strategy and a detailed analysis of 1 H NMR data will be discussed. Select compounds included in this work were screened against the NCI60 cell line panel and displayed modest growth inhibition activity.

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Section: Resultsmentioning

confidence: 99%

Asymmetric Total Synthesis and Revision of Absolute Stereochemistry for (+)-Taumycin A: An Approach that Exploits Orthogonally Protected Quasienantiomers

Shrestha¹,

Golliher²,

Newar³

et al. 2021

J. Org. Chem.

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A general and concise stereodivergent chiral pool approach toward trans-(4S,5R)- and cis-(4R,5R)-5-alkyl-4-methyl-γ-butyrolactones: Syntheses of (+)-trans- and (+)-cis-whisky and cognac lactones from d-(+)-mannitol

Manna

Chakraborty

Chatterjee

et al. 2021

Carbohydrate Research

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Terpenoids from Alpinia galanga and their acetylcholinesterase inhibitory activity

Zhou,

Guo,

Zhao

et al. 2024

Natural Product Research

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A new labdane diterpene (1), two new norsesquiterpenoids (2-3), as well as eight known terpenoids (4-11) were isolated from the seeds of Alpinia galanga (Zingiberaceae). Their structures and absolute configurations were elucidated by 1D, 2D NMR, MS, and comparison of their experimental and calculated electronic circular dichroism (ECD). The acetylcholinesterase (AChE) inhibitory activities of all the isolated compounds (1-11) were evaluated and the result showed that compounds 6 and 9 had inhibitory activity against AChE, with IC 50 values at 295.70 and 183.91 μM, whereas other compounds did not show any inhibitory activity.

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Enantiodivergent syntheses of (+)- and (−)-1-(2,6-dimethylphenoxy)propan-2-ol: A way to access (+)- and (−)-mexiletine from D-(+)-mannitol

Cited by 3 publications

References 55 publications

Asymmetric Total Synthesis and Revision of Absolute Stereochemistry for (+)-Taumycin A: An Approach that Exploits Orthogonally Protected Quasienantiomers

Asymmetric Total Synthesis and Revision of Absolute Stereochemistry for (+)-Taumycin A: An Approach that Exploits Orthogonally Protected Quasienantiomers

A general and concise stereodivergent chiral pool approach toward trans-(4S,5R)- and cis-(4R,5R)-5-alkyl-4-methyl-γ-butyrolactones: Syntheses of (+)-trans- and (+)-cis-whisky and cognac lactones from d-(+)-mannitol

Terpenoids from Alpinia galanga and their acetylcholinesterase inhibitory activity

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