Facile Access to <i>cis</i>‐2,6‐Disubstituted Tetrahydropyrans by Palladium‐Catalyzed Decarboxylative Allylation: Total Syntheses of (±)‐Centrolobine and (+)‐Decytospolides A and B

Zeng, Jing; Tan, Yu; Ma, Jimei; Leow, Min Li; Tirtorahardjo, Davin; Liu, Xuewei

doi:10.1002/chem.201303328

Cited by 35 publications

(19 citation statements)

References 121 publications

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“…[6] When the resulting b-keto amide 9 was subjected to phosphorus oxychloride,asmooth cyclization occurred that proceeded with complete diastereoselectivity. [6] When the resulting b-keto amide 9 was subjected to phosphorus oxychloride,asmooth cyclization occurred that proceeded with complete diastereoselectivity.…”

supporting

confidence: 74%

Total Synthesis of Crocagin A

Bihelovic¹,

Stichnoth²,

Müller³

et al. 2017

Angewandte Chemie

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Crocagin A( 1)c ombines an attractive molecular structure with an unusual biosynthesis and bioactivity.A n efficient synthesis of crocagin Aispresented that hinges on an early formation of the heterotricyclic core,a ne lectrophilic amination, and the stereoselective hydrogenation of atetrasubstituted double bond. This synthesis confirms the absolute configuration of crocagin Aand provides access to the natural product and derivatives thereof for further biological testing. Scheme 1. Structure and biosynthetic origin of crocagin.Scheme 2. Retrosynthetic analysis of crocagin A.

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supporting

confidence: 74%

Total Synthesis of Crocagin A

Bihelovic¹,

Stichnoth²,

Müller³

et al. 2017

Angewandte Chemie

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“…Our actual synthesis began with the coupling of dtryptophan methyl ester (7)a nd the known aryl b-keto acid 8 (Scheme 3). [6] When the resulting b-keto amide 9 was subjected to phosphorus oxychloride,asmooth cyclization occurred that proceeded with complete diastereoselectivity. [7] Ther elative configuration of the heterotricyclic product 10 was initially deduced by 1 H-NMR spectroscopy based on the chemical shift of the carbomethoxy group (3.8 ppm).…”

mentioning

confidence: 99%

Total Synthesis of Crocagin A

et al. 2017

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Crocagin A (1) combines an attractive molecular structure with an unusual biosynthesis and bioactivity. An efficient synthesis of crocagin A is presented that hinges on an early formation of the heterotricyclic core, an electrophilic amination, and the stereoselective hydrogenation of a tetrasubstituted double bond. This synthesis confirms the absolute configuration of crocagin A and provides access to the natural product and derivatives thereof for further biological testing.

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“…mp 93°C–94°C. 7 1 H NMR (600 MHz, CDCl 3 ) δ 7.92 (d, J =8.9 Hz, 2H), 7.44–7.36 (m, 4H), 7.34 (d, J =7.2 Hz, 1H), 6.99 (d, J =8.9 Hz,2H), 5.11 (s, 2H), 2.54 (s, 3H); 13 C NMR (151 MHz, CDCl 3 ) δ 196.74, 162.57, 136.13, 130.57, 130.48, 128.67, 128.22, 127.44, 114.50, 70.10, 26.34; APCI-HRMS m/z: calcd for C H + 15 15O2 (MH), 227.1067, found 227.1063.…”

Section: Supplementary Materialsmentioning

confidence: 99%

2-acetylphenol analogs as potent reversible monoamine oxidase inhibitors

Legoabe

Petzer

2015

DDDT

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Based on a previous report that substituted 2-acetylphenols may be promising leads for the design of novel monoamine oxidase (MAO) inhibitors, a series of C5-substituted 2-acetylphenol analogs (15) and related compounds (two) were synthesized and evaluated as inhibitors of human MAO-A and MAO-B. Generally, the study compounds exhibited inhibitory activities against both MAO-A and MAO-B, with selectivity for the B isoform. Among the compounds evaluated, seven compounds exhibited IC50 values <0.01 µM for MAO-B inhibition, with the most selective compound being 17,000-fold selective for MAO-B over the MAO-A isoform. Analyses of the structure–activity relationships for MAO inhibition show that substitution on the C5 position of the 2-acetylphenol moiety is a requirement for MAO-B inhibition, and the benzyloxy substituent is particularly favorable in this regard. This study concludes that C5-substituted 2-acetylphenol analogs are potent and selective MAO-B inhibitors, appropriate for the design of therapies for neurodegenerative disorders such as Parkinson’s disease.

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Facile Access to cis‐2,6‐Disubstituted Tetrahydropyrans by Palladium‐Catalyzed Decarboxylative Allylation: Total Syntheses of (±)‐Centrolobine and (+)‐Decytospolides A and B

Cited by 35 publications

References 121 publications

Total Synthesis of Crocagin A

Total Synthesis of Crocagin A

Total Synthesis of Crocagin A

2-acetylphenol analogs as potent reversible monoamine oxidase inhibitors

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