Dibromomethane as One‐Carbon Source in Organic Synthesis: Formal Total Synthesis of (±)‐Nephrosteranic Acid

Hon, Yung‐Son; Hsieh, Chia-Lung; Chen, Hsien-Fan

doi:10.1080/00397910701263767

Cited by 12 publications

(2 citation statements)

References 39 publications

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“…After evaporation of the solvent, the crude was purified by silica gel chromatography using a light petroleum ether/EtOAc 6/1 to give the product 12 (0.75 mmol, 75% yield from 3 ). The spectroscopic data of 12 matched the ones reported in the literature ( Hon et al, 2007 ). 1 H-NMR (CDCl 3 ) δ 4.02 (m, 1H), 3.73 (s, 3H), 2.53 (dd, J = 3 Hz, 16.4 Hz, 1H), 2.43 (dd, J = 9.1 Hz, 16.4 Hz, 1H), 1.57-1.29 (m, 20H), 0.90 (t, J = 6.8 Hz, 3H).…”

Section: Methodssupporting

confidence: 81%

Facile and Sustainable Synthesis of Commendamide and its Analogues

2022

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Commendamide, or N-(3-hydroxypalmitoyl)-glycine 1a, is a gut microbiota-derived bioactive metabolite, structurally similar to long-chain N-acyl-amino acids which belong to the complex lipid signaling system known as endocannabinoidome and play important roles in mammals through activation of, inter alia, G-protein-coupled receptors (GPCRs). In this work, we describe a simple, green and economic method for the preparation of commendamide 1a, a GPCR G2A/132 agonist. The developed protocol is general and could also be applied to the synthesis of deuterated commendamide 1b, as well as to other minor microbiota-derived metabolites, such as the analog 2.

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Section: Methodssupporting

confidence: 81%

Facile and Sustainable Synthesis of Commendamide and its Analogues

2022

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“…The synthesis was quite efficient and completed in steps with 69.3% overall yield. Hon and co-workers [60] in achieved the diastereoselective formal synthesis of (�)-nephrosteranic acid (Scheme 37). The Reformatsky reaction on dodecanal 177 gave the β-hydroxy ester, which on Frater's [61] allylation resulted in 178.…”

Section: Nephrosteranic Acid (4 A) and Roccellaric Acid (4 B)mentioning

confidence: 99%

Evolution of Strategies in Paraconic Acids Synthesis

2020

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Various syntheses of different paraconic acids over the last seventeen years have been abstracted here. Paraconic acids have either a methylene or methyl group at the 4-position of the γ-butyrolactone with a common C-3 carboxylic acid group and a long alkyl chain. Several possibilities of relative configurations give rise to distinct set of paraconic acids, which are also categorized in this review. Various strategies based on chiral catalytic methods, chiral pool, chiral auxiliary, resolution and other methods were engaged in the synthesis of different paraconic acids. A few members are yet to be synthesized and this compilation might entice future synthetic attempts on them.

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Total Synthesis of Nominal Gobienine A

Kondoh

Andrejew

Gabor

et al. 2013

Chemistry A European J

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The lichen-derived glycoconjugate gobienine A is structurally more complex than most glycolipids isolated from higher plants by virtue of the all-cis substituted γ-lactone substructure embedded into its macrocyclic frame. A concise entry into this very epimerization-prone and hence challenging structural motif is presented, which relies on an enantioselective cyanohydrin formation, an intramolecular Blaise reaction, a palladium-catalyzed alkoxycarbonylation, and a diastereoselective hydrogenation of the tetrasubstituted alkene in the resulting butenolide. This strategy, in combination with ring-closing olefin metathesis for the formation of the macrocyclic perimeter, allowed the proposed structure of gobienine A (1) to be formed in high overall yield. The recorded spectral data show that the structure originally attributed to gobienine A is incorrect and that it is not the epimerization-prone ester site on the butanolide ring that is the locus of misassignment; rather, the discrepancy must be more profound.

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Dibromomethane as One‐Carbon Source in Organic Synthesis: Formal Total Synthesis of (±)‐Nephrosteranic Acid

Cited by 12 publications

References 39 publications

Facile and Sustainable Synthesis of Commendamide and its Analogues

Facile and Sustainable Synthesis of Commendamide and its Analogues

Evolution of Strategies in Paraconic Acids Synthesis

Total Synthesis of Nominal Gobienine A

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