- 4-Heterosubstituted Cyclopentenone Antiviral Compounds: Synthesis, Mechanism, and Antiviral Evaluation
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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).
- Mantione, Daniele,Aizpuru, Olatz Olaizola,Memeo, Misal Giuseppe,Bovio, Bruna,Quadrelli, Paolo
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p. 983 - 991
(2016/03/01)
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- Enantioselective synthesis of 4-heterosubstituted cyclopentenones
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Racemic 4-hydroxycyclopentenone, readily derived from furfuryl alcohol, can be transformed via its O-Boc derivative to 4-acyloxy, 4-aryloxy-, 4-amino-, or 4-thio-substituted cyclopentenones with high enantioselectivity by palladium-catalyzed kinetic resolution via nucleophilic allylic substitutions. Applying this methodology, a short formal synthesis of ent-noraristeromycin was readily accomplished.
- Ulbrich, Kathrin,Kreitmeier, Peter,Vilaivan, Tirayut,Reiser, Oliver
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p. 4202 - 4206
(2013/06/04)
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- Enzymatic kinetic resolution studies of racemic 4-hydroxycyclopent-2-en- 1-one using Lipozyme IM
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Enzymatic kinetic resolution studies of (±)-4-hydroxycyclopent-2-en-1- one 2 were taken up in organic solvents by transesterification with vinyl acetate and alcoholysis of its acetate 3 as an alternative to the desymmetrization of meso-cyclopentenediol to provide faster and economic access to enantiomerically pure 4-(R)-tert-butyldimethylsilyloxycyclopent-2- en-1-one 1. Parameters were screened using Lipozyme IM as catalyst. Although enantioselectivity observed was moderate (E=24, by alcoholysis of 3 with 2-butanol), trends in the effect of solvent, water content and alcohol structure showed useful directions for screening of other enzymes for optimization of the method to useful levels of efficiency.
- Ghorpade, Sandeep R.,Bastawade, Kulbhushan B.,Gokhale, Digambar V.,Shinde, Popat D.,Mahajan, Vishal A.,Kalkote, Uttam R.,Ravindranathan
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p. 4115 - 4122
(2007/10/03)
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- A Novel Asymmetric Synthesis of Chiral Cyclopentanoid Building Blocks by the Use of Chiral Lithium Amide
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Enantioselective deprotonation of meso-epoxides, derived from 3-cyclopenten-1-ol, was examined using chiral lithium amide.Chiral cis-4-t-butyldimethylsiloxy-2-cyclopenten-1-ol, cis-4-tetrahydropyranyloxy-2-cyclopenten-1-ol, and their trans-isomers, which are useful chiral building blocks for the synthesis of cyclopentanoid natural compounds, were obtained with high enantiomeric excesses (72 - 90 percent ee).Both (R)- and (S)-4-hydroxy-2-cyclopenten-1-one were derived from (1S,4R)-4-t-butyldimethylsiloxy)-2-cyclopenten-1-ol stereospecifically.
- Asami, Masatoshi
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p. 1402 - 1408
(2007/10/02)
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- AN ASYMMETRIC SYNTHESIS OF CIS-4-t-BUTYLDIMETHYLSILOXY-2-CYCLOPENTEN-1-OL AND CIS-4-TETRAHYDROPYRANYLOXY-2-CYCLOPENTEN-1-OL, VERSATILE CHIRAL SYNTHETIC INTERMEDIATE FOR PROSTANOIDS
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cis-4-t-Butyldimethylsiloxy-2-cyclopenten-1-ol and cis-4-tetrahydropyranyloxy-2-cyclopenten-1-ol were obtained with high enantiomeric excesses (ee) by the reaction of cis-3,4-epoxycyclopentan-1-ol derivatives with chiral lithium amide.An application to the syntheses of both (S)- and (R)-4-hydroxy-2-cyclopentenone was demonstrated.
- Asami, Masatoshi
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p. 5803 - 5806
(2007/10/02)
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