Enantioselective Synthesis of 4-Heterosubstituted Cyclopentenones

Ulbrich, Kathrin; Kreitmeier, Peter; Vilaivan, Tirayut; Reiser, Oliver

doi:10.1021/jo400409f

Cited by 41 publications

(31 citation statements)

References 45 publications

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“…Regioisomeric adducts 15 and 16 were obtained in moderate yields in a 73:27 ratio. The structure of adduct 15 was found to be identical to that reported in the literature,10 while the structure of its regioisomer 16 was assigned on the basis of analytical and spectroscopic data.…”

Section: Resultssupporting

confidence: 69%

“…The residue was submitted to chromatographic separation to isolate the products. Adduct 15 was found to be identical to the product described in the literature,10 while its regioisomer 16 was fully characterized.…”

Section: Methodsmentioning

confidence: 55%

“…Racemic 4‐oxocyclopent‐2‐en‐1‐yl acetate [(±)‐ 10 ] was prepared by acetylation12 of 4‐hydroxy‐2‐cyclopentenone [(±)‐ 9 ]10,13 in the presence of acetic anhydride and pyridine in THF as solvent.…”

Section: Resultsmentioning

confidence: 99%

“…The chemistry of this scaffold has been extensively investigated and reviewed, as the hydroxycyclopentenone moiety often appears in natural products and biologically active compounds, or constitutes the privileged starting material for their synthesis 9. Recently, Reiser and co‐workers used the chemistry of 4‐hydroxy‐2‐cyclopentenone for the enantioselective synthesis of ent ‐norarisateromycin10 and other enantiopure guaianes and pseudoguaianolides 11…”

Section: Introductionmentioning

confidence: 99%

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4‐Heterosubstituted Cyclopentenone Antiviral Compounds: Synthesis, Mechanism, and Antiviral Evaluation

et al. 2016

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Racemic 4‐oxocyclopent‐2‐en‐1‐yl acetate was used in a short synthesis of nucleoside analogues with pyrimidine and purine heterobases. The protocol is based on a typical nucleophilic substitution process. Uracil, thymine, 6‐chloropurine, and some adenines gave the expected 4‐heterosubstituted products along with the isomeric 2‐heterosubstituted compounds as minor components. Samples of selected products were evaluated for their antiviral activity in a primary screening against a variety of viruses belonging to different classes. One of the compounds was found to be highly active against human papilloma virus (HPV).

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Section: Resultssupporting

confidence: 69%

Section: Methodsmentioning

confidence: 55%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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4‐Heterosubstituted Cyclopentenone Antiviral Compounds: Synthesis, Mechanism, and Antiviral Evaluation

et al. 2016

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“…Furfuryl alcohol is also the source of 4-hydroxy-2-cyclopentenone, which, in enantiopure form, has been used as an intermediate for the synthesis of natural products and pharmaceutical drugs [ 3 ]. Recently, racemic (+/−)-4-hydroxy-2-cyclopentenone has found application in the synthesis of nucleoside analogues [ 4 – 5 ] and some of the products have shown interesting antiviral activities. As part of our studies on carbocyclic nucleoside phosphonates [ 6 ] as potential anti-HIV agents [ 7 – 8 ], we envisioned to use bio-sourced racemic (+/−)-4- O -protected 2-cyclopentenone for the synthesis of hitherto unknown carbocyclic nucleoside methylphosphonates ( Fig.…”

Section: Introductionmentioning

confidence: 99%

Revaluation of biomass-derived furfuryl alcohol derivatives for the synthesis of carbocyclic nucleoside phosphonate analogues

Mohamed¹,

Philouze²,

Mathé³

2017

Beilstein J. Org. Chem.

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The racemic synthesis of new carbocyclic nucleoside methylphosphonate analogues bearing purine bases (adenine and guanine) was accomplished using bio-sourced furfuryl alcohol derivatives. All compounds were prepared using a Mitsunobu coupling between the heterocyclic base and an appropriate carbocyclic precursor. After deprotection, the compounds were evaluated for their activity against a large number of viruses. However, none of them showed significant antiviral activity or cytotoxicity.

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pseudo Enantiomeric Carbohydrate Olefin Ligands – Case Study and Application in Kinetic Resolution in Rhodium(I)‐Catalysed 1,4‐Addition

2014

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In order to investigate significant differences in asymmetric induction for pseudo enantiomeric carbohydrate olefin ligands in rhodium(I)catalysed 1,4-addition reactions, we designed a set of new olefin ligands differing in relative configuration and pyranoside conformation. With these, we have successfully elucidated structural requirements for metal binding and also identified an improved alternative for one pseudo enantiomer. Furthermore, we report the efficient kinetic resolution of a racemic 4-hydroxycyclopentenone derivative by 1,4-addition.Due to the increasing demand for chiral building blocks in natural product and medicinal chemistry, the design of new chiral ligands for asymmetric metal catalysis is an active research field. Chiral olefin ligands, [1] introduced independently by Hayashi [2] and Carreira, [3] are the ligands of choice for rhodium(I)mediated 1,4-additions of boronic acids to enones. [4] Carbohydrates are attractive, inexpensive starting materials for the design of novel ligands. [5] With gluco-enoPhos (1a, 1aa) [6] and galacto-enoPhos (psent-1a), [7] we have introduced a set of pseudo enantiomeric [8] olefin-phosphinite ligands derived from d-glucose and d-galactose (Scheme 1), giving 1,4-addition products in opposite configurations and typically above 90% ee. Significantly lower selectivity was observed for the gluco-ligands 1a and 1aa with bulky arylboronic and alkenylboronic acids, while high ees were retained with galacto-ligand ps-ent-1a. [7] This finding prompted us to investigate the origin of the differing asymmetric induction exerted by 1a and 1aa on the one hand and ps-ent-1a on the other hand, as well as to develop an improved alternative to gluco-ligands 1a and 1aa.An obvious explanation for the different efficiency of the gluco-ligands (1a, 1aa) and galacto-ligand (ps-Scheme 1. Ligands gluco-enoPhos (1a and 1aa) and galacto-enoPhos (ps-ent-1a): proposed coordination to Rh(I).

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Enantioselective Synthesis of 4-Heterosubstituted Cyclopentenones

Cited by 41 publications

References 45 publications

4‐Heterosubstituted Cyclopentenone Antiviral Compounds: Synthesis, Mechanism, and Antiviral Evaluation

4‐Heterosubstituted Cyclopentenone Antiviral Compounds: Synthesis, Mechanism, and Antiviral Evaluation

Revaluation of biomass-derived furfuryl alcohol derivatives for the synthesis of carbocyclic nucleoside phosphonate analogues

pseudo Enantiomeric Carbohydrate Olefin Ligands – Case Study and Application in Kinetic Resolution in Rhodium(I)‐Catalysed 1,4‐Addition

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