The first stereoselective non-biological synthesis of chiral 6-pentyl-2 H -pyran-2-ones: total synthesis of metabolites isolated from Trichoderma spp and Penicillium isolates

Pérez-Bautista, José Alvano; Meza-León, Rosa L.; Cruz‐Gregorio, Silvano; Quintero, Leticia; Sartillo‐Piscil, Fernando

doi:10.1016/j.tetlet.2016.08.089

Cited by 7 publications

(6 citation statements)

References 21 publications

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“…Previously, starting from the versatile chiron 7,3-lactone-xylofuranose ( 7,3-LXF ) [ 6 ], the first non-biological synthesis of chiral 6-pentyl-2 H -pyran-2-ones 1 – 3 was reported by our research group [ 7 ]. These molecules proved to be enantiomers of metabolites isolated from Trichoderma spp and Penicillium isolates .…”

Section: Resultsmentioning

confidence: 99%

“…Cyclic thiocarbonate 6 was prepared in two steps from pyrone dioxolane 7 [ 7 ]. Acid hydrolysis of 7 to 1,2-diol 8 followed by the reaction with 1,1’-thiocarbonyldiimidazole afforded thiocarbonate precursor 6 in high overall yield ( Scheme 3 ).…”

Section: Resultsmentioning

confidence: 99%

“…Acid hydrolysis of 7 to 1,2-diol 8 followed by the reaction with 1,1’-thiocarbonyldiimidazole afforded thiocarbonate precursor 6 in high overall yield ( Scheme 3 ). Compounds 6 and 8 were prepared in a similar manner as described in reference [ 7 ].…”

Section: Resultsmentioning

confidence: 99%

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Electrochemical Corey–Winter reaction. Reduction of thiocarbonates in aqueous methanol media and application to the synthesis of a naturally occurring α-pyrone

López-López¹,

Pérez-Bautista²,

Sartillo‐Piscil³

et al. 2018

Beilstein J. Org. Chem.

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An electrochemical version of the Corey–Winter reaction was developed giving excellent results in aqueous methanol media (MeOH/H2O (80:20) with AcOH/AcONa buffer 0.5 M as supporting electrolyte), using a reticulated vitreous carbon as cathode in a divided cell. The electrochemical version is much more environmentally friendly than the classical reaction, where a large excess of trialkyl phosphite as reducing agent and high temperatures are required. Thus, cathodic reduction at room temperature of two cyclic thiocarbonates (−1.2 to −1.4 V vs Ag/AgCl) afforded the corresponding alkenes, trans-6-(pent-1-enyl)-α-pyrone and trans-6-(pent-1,4-dienyl)-α-pyrone, which are naturally occurring metabolites isolated from Trichoderma viride and Penicillium, in high chemical yield and with excellent stereo selectivity.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Electrochemical Corey–Winter reaction. Reduction of thiocarbonates in aqueous methanol media and application to the synthesis of a naturally occurring α-pyrone

López-López¹,

Pérez-Bautista²,

Sartillo‐Piscil³

et al. 2018

Beilstein J. Org. Chem.

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“…The current synthetic strategy for (+)‐ 4 is based on the application of the SHOWO protocol (sequential hydrolysis/oxidation/Wittig olefination) to 6 , giving first the lactam 7 , which is then stereoselectively dihydroxylated and transformed into the title compound by further manipulations of the furanose ring (Scheme ). A stereoselective version of the SHOWO protocol has been successfully employed for the synthesis of the versatile chiron 8 (also known as 7,3‐LXF) starting from diacetone‐D‐glucose (DAG) . Since the success of the stereoselective SHOWO protocol is attributed to the presence of the free hydroxyl group in DAG, which is responsible for the high Z ‐selectivity, we anticipated that the amine group in 6 would behave similarly, thus allowing the preparation of the unsaturated lactam 7 (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Straighforward Synthesis of a Novel Chiron and its Application to the Synthesis of (+)‐1,4‐Dideoxymannojirimycin and Further Polyoxygenated 2‐Pyperidones

et al. 2017

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The total synthesis of (+)-1,4-dideoxymannojimycin and the enantiopure synthesis of three polyoxygenated piperidin-2ones from a novel chiron is reported. Starting from 3-deoxy-3amine-D-glucose, by means of the stereoselective aqueous SHOWO protocol (Sequential-Hydrolysis-Oxidation-Wittig Olefination), the unsaturated-7,3-lactam-D-xylofuranose derivative was prepared, which depending on the oxidative C À C bond cleavage reaction conditions for the furanose moiety, is transformed into either (+)-1,4-dideoxymannojirimycin or polyoxygenated piperidin-2-ones.The authors declare no conflict of interest.

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“…The Chiron known as 7,3-LXF (7,3-lactone-xylofuranose derivative; Ramírez et al, 2017), derived from d-glucose, is a versatile starting material for the synthesis of natural products, for example the metabolites produced by Trichoderma spp and Penicillium data reports isolates (Pé rez-Bautista et al, 2016). In a work aimed at the synthesis of 1-deoxynojirimycin (DNJ), an azasugar alkaloid presenting -glucosidase inhibitor properties, the title compound was obtained (Amaro Herná ndez, 2019).…”

Section: Structure Descriptionmentioning

confidence: 99%

Ethyl (3S)-3-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[4,5-d][1,3]dioxol-5-yl]-3-{(3S)-3-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[4,5-d][1,3]dioxol-5-yl]-5-oxoisoxazolidin-2-yl}propanoate chloroform monosolvate

et al. 2020

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The title compound, C22H33NO12·CHCl3, was obtained as a product of a double aza-Michael addition of hydroxylamine on a Chiron with a known absolute configuration. The enantiopure compound crystallized as a chloroform solvate, in space group P1, and diffraction data were collected at room temperature with Ag Kα radiation. The Flack parameter refined to x = −0.01 (16); however, the Flack and Watkin 2AD plot clearly shows that differences between Friedel opposites (the D component of the plot) do not carry any reliable information about resonant scattering of Cl atoms, and are rather dominated by random and systematic errors. The RD factor calculated using 1941 acentric Friedel pairs is RD = 0.995. On the other hand, the 2A component of the plot, related to average intensities of Friedel pairs, shows that data are of good quality (RA = 0.069). This example illustrates that while using Ag Kα radiation (λ = 0.56083 Å), scatterers heavier than Cl should be present in a chiral crystal in order to determine confidently the absolute structure of the crystal.

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The first stereoselective non-biological synthesis of chiral 6-pentyl-2 H -pyran-2-ones: total synthesis of metabolites isolated from Trichoderma spp and Penicillium isolates

Cited by 7 publications

References 21 publications

Electrochemical Corey–Winter reaction. Reduction of thiocarbonates in aqueous methanol media and application to the synthesis of a naturally occurring α-pyrone

Electrochemical Corey–Winter reaction. Reduction of thiocarbonates in aqueous methanol media and application to the synthesis of a naturally occurring α-pyrone

Straighforward Synthesis of a Novel Chiron and its Application to the Synthesis of (+)‐1,4‐Dideoxymannojirimycin and Further Polyoxygenated 2‐Pyperidones

Ethyl (3S)-3-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[4,5-d][1,3]dioxol-5-yl]-3-{(3S)-3-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[4,5-d][1,3]dioxol-5-yl]-5-oxoisoxazolidin-2-yl}propanoate chloroform monosolvate

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