First Total Synthesis of Prorepensin with a Bis-Geranylated Chalcone

doi:10.5012/bkcs.2009.30.11.2563

Cited by 2 publications

(1 citation statement)

References 17 publications

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“…Under standard conditions benzyl alcohol 22 (1.05 g, 3.4 mmol) in CH 2 Cl 2 (14 mL) was treated with TBSCl (0.729 g, 4.8 mmol) and imidazole (0.712 g, 10.5 mmol). After 2 h, the usual workup provided silyl compound 28 (1.23 g, 85%) as a clear oil, and the 1 H NMR spectrum matched known data. , …”

Section: Experimental Sectionmentioning

confidence: 65%

Selective Prenylation of Protected Phenols for Synthesis of Pawhuskin A Analogues

Gardner

Wiemer

2016

J. Org. Chem.

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Pawhuskin A is a prenylated stilbene that functions as an antagonist of the kappa opioid receptor. Analogues of this natural product bearing different placements of the prenyl group in the A-ring have shown selectivity for either the kappa or the delta receptors subtypes. This differential activity has drawn attention to regiospecific preparation of the C-2, C-5, and C-6 prenylated A-ring regioisomers. Through halogen metal exchange, advanced intermediates representing each of these regioisomers have been prepared, and the new C-6 intermediate has been converted to a new analogue of the natural stilbene.

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Section: Experimental Sectionmentioning

confidence: 65%

Selective Prenylation of Protected Phenols for Synthesis of Pawhuskin A Analogues

Gardner

Wiemer

2016

J. Org. Chem.

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Secondary metabolites, their structural diversity, bioactivity, and ecological functions: An overview

Abegaz

Kinfe

2019

Physical Sciences Reviews

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Abstract Natural products are also called secondary metabolites to distinguish them from the primary metabolites, i.e. those natural compounds like glucose, amino acids, etc. that are present in every living cell and are used and required in the essential life processes of cells. Natural products are classified according to their metabolic building blocks into alkaloids, fatty acids, polyketides, phenyl propanoids and aromatic polyketides, and terpenoids. The structural diversity of natural products is explored using the scaffold approach focusing on the characteristic carbon frameworks. Aside from discussing specific alkaloids that are either pharmacologically (e.g. boldine, berberine, galantamine, etc.) or historically (caffeine, atropine, lobeline, etc.) important alkaloids, a single chart is presented which shows the typical scaffolds of the most important subclasses of alkaloids. How certain classes of natural products are formed in nature from simple biochemical ‘building blocks’ are shown using graphical schemes. This has been done for a typical tetra-ketide (6-methylsalicylic acid) from acetyl coenzyme A, or in general to all the major subclasses of terpenes. An important aspect of understanding the structural diversity of natural products is to recognize how some compounds can be visualized as key intermediates for enzyme mediated transformation to several other related structures. This is seen in the case of how arachidonic acid can transform into prostaglandins, or geranyl diphosphate to various monoterpenes, or squalene epoxide to various pentacyclic triterpenes, or cholesterol transforming to sex hormones, bile acids and the cardioactive cardenolides and bufadienolides. These are presented in carefully designed schemes and charts that are appropriately placed in the relevant sections of the narrative texts. The ecological functions and pharmacological properties of natural products are also presented showing wherever possible how the chemical scaffolds have led to developing drugs as well as commercial products like sweeteners.

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First Total Synthesis of Prorepensin with a Bis-Geranylated Chalcone

Cited by 2 publications

References 17 publications

Selective Prenylation of Protected Phenols for Synthesis of Pawhuskin A Analogues

Selective Prenylation of Protected Phenols for Synthesis of Pawhuskin A Analogues

Secondary metabolites, their structural diversity, bioactivity, and ecological functions: An overview

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