Total synthesis of the pseudopterosin aglycones

Newton, Christopher G.; Sherburn, Michael S.

doi:10.1039/c5np00008d

Cited by 24 publications

(19 citation statements)

References 83 publications

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“…Therefore, the tricyclic planar structure of 1 was assigned as shown to possess a hexahydro-1 H -phenalene ring system. The carbons in compound 1 were numbered according to the precedent pseudopterosins [ 11 ]. The structure of 1 is recognized as a new amphilectane-type diterpenoid [ 12 , 13 ], and the name acrepseudoterin is proposed for compound 1 .…”

Section: Resultsmentioning

confidence: 99%

PTP1B Inhibitory Secondary Metabolites from an Antarctic Fungal Strain Acremonium sp. SF-7394

Kim

et al. 2021

Molecules

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Chemical investigation of the Antarctic lichen-derived fungal strain Acremonium sp. SF-7394 yielded a new amphilectane-type diterpene, acrepseudoterin (1), and a new acorane-type sesquiterpene glycoside, isocordycepoloside A (2). In addition, three known fungal metabolites, (−)-ternatin (3), [D-Leu]-ternatin (4), and pseurotin A (5), were isolated from the EtOAc extract of the fungal strain. Their structures were mainly elucidated by analyzing their NMR and MS data. The absolute configuration of 1 was proposed by electronic circular dichroism calculations, and the absolute configuration of the sugar unit in 2 was determined by a chemical method. The inhibitory effects of the isolated compounds on protein tyrosine phosphatase 1B (PTP1B) were evaluated by enzymatic assays; results indicated that acrepseudoterin (1) and [D-Leu]-ternatin (4) dose-dependently inhibited the enzyme activity with IC50 values of 22.8 ± 1.1 μM and 14.8 ± 0.3 μM, respectively. Moreover, compound 1 was identified as a competitive inhibitor of PTP1B.

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Section: Resultsmentioning

confidence: 99%

PTP1B Inhibitory Secondary Metabolites from an Antarctic Fungal Strain Acremonium sp. SF-7394

Kim

et al. 2021

Molecules

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“…(Figure ) . Consequently, intensive efforts have been continuously devoted in the last three decades to the asymmetric syntheses of these natural products . Despite the seemingly simple structures, there are significant challenges in 1) controlling the relative and absolute stereochemistry for constructing these nonpolar stereogenic centers and 2) synthesizing penta‐ and hexasubstituted benzene rings in most of these natural products.…”

Section: Resultsmentioning

confidence: 99%

Asymmetric Total Syntheses of Di‐ and Sesquiterpenoids by Catalytic C−C Activation of Cyclopentanones

et al. 2020

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To show the synthetic utility of the catalytic C−C activation of less strained substrates, described here are the collective and concise syntheses of the natural products (−)‐microthecaline A, (−)‐leubehanol, (+)‐pseudopteroxazole, (+)‐seco‐pseudopteroxazole, pseudopterosin A–F and G—J aglycones, and (+)‐heritonin. The key step in these syntheses involve a Rh‐catalyzed C−C/C−H activation cascade of 3‐arylcyclopentanones, which provides a rapid and enantioselective route to access the polysubstituted tetrahydronaphthalene cores presented in these natural products. Other important features include 1) the direct C−H amination of the tetralone substrate in the synthesis of (−)‐microthecaline A, 2) the use of phosphoric acid to enhance efficiency and regioselectivity for problematic cyclopentanone substrates in the C−C activation reactions, and 3) the direct conversion of serrulatane into amphilectane diterpenes by an allylic cyclodehydrogenation coupling.

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“…A substituted 1,1‐divinylallene precursor recently delivered the shortest step count total synthesis of pseudopterosin natural products (Figure ) . The brevity of the synthesis is all the more surprising, since more C−C bonds, rings and stereocenters are forged than other syntheses …”

Section: Figurementioning

confidence: 99%

Tetravinylallene

2019

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The first chemical synthesis of tetravinylallene (3,5‐divinylhepta‐1,3,4,6‐tetraene) is reported. The final, key step of the synthesis involves a palladium‐catalyzed, Negishi‐type cross‐coupling involving 1,5‐transposition of a penta‐2‐en‐4‐yn‐1‐ol methanesulfonate. The unprecedented fundamental hydrocarbon is sufficiently stable to be purified by flash chromatography. A similar synthetic pathway grants access to the first substituted tetravinylallenes, which provide insights into the influence of substitution upon stability and reactivity. Tetravinylallenes are shown to break new ground in swift structural complexity creation, with three novel sequences reported.

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Total synthesis of the pseudopterosin aglycones

Cited by 24 publications

References 83 publications

PTP1B Inhibitory Secondary Metabolites from an Antarctic Fungal Strain Acremonium sp. SF-7394

PTP1B Inhibitory Secondary Metabolites from an Antarctic Fungal Strain Acremonium sp. SF-7394

Asymmetric Total Syntheses of Di‐ and Sesquiterpenoids by Catalytic C−C Activation of Cyclopentanones

Tetravinylallene

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