The Experts below are selected from a list of 360 Experts worldwide ranked by ideXlab platform
Rossi Renzo - One of the best experts on this subject based on the ideXlab platform.
-
An Economical Access to 3,4-Diaryl-2(5H)-furanones and 4-Aryl-6-methyl-2(2H)-pyranones via Pd-Catalyzed Suzuki-Type Arylation of 3-Aryl-4-tosyloxy-2(5H)-furanones and 6-Methyl-4-tosyloxy-2(2H)-pyranones, Respectively
'Wiley', 2009Co-Authors: Rossi Renzo, Bellina Fabio, Marchetti ChiaraAbstract:Both symmetrical and unsymmetrical 3,4-diaryl-substituted 2(5H)-furanones have been efficiently synthesized using an inexpensive procedure involving the Pd(OAc)2/PCy3-catalyzed Suzuki-type arylation of readily available 3-aryl-4-tosyloxy-2(5H)-furanones as the key step. The mild conditions of this arylation protocol have also been used for the high yielding synthesis of 4-aryl-6-methyl-2(2H)-pyranones from 6-methyl-4-tosyloxy-2(2H)-pyranone
-
6-Chloro-2(2H)-pyranone: a new 2(2H)-pyranone synthon
'Elsevier BV', 2003Co-Authors: Biagetti M., Bellina Fabio, Carpita Adriano, Rossi RenzoAbstract:6-Chloro-2(2H)-pyranone, which can be prepd. in high yield from com. available trans-glutaconic acid, undergoes facile Pd/Cu-catalyzed reaction with various 1-alkynes to give rise to the corresponding 6-(1-alkynyl)-2(2H)-pyranones in moderate to good yields. These last hitherto unknown compds. were used as direct precursors to 6-alkyl- and 6-[(Z)-1-alkenyl]-2(2H)-pyranones
-
Selective synthesis of 5,6-disubstituted 3-methyl-2(2H)-pyranones and 6-substituted 3-methyl-2(2H)-pyranones, including fusalanipyrone and gibepyrone A
'Wiley', 2002Co-Authors: Biagetti M., Bellina Fabio, Carpita Adriano, Viel S, Mannina L, Rossi RenzoAbstract:The 6-substituted 3-bromo-5-iodo-2(2H)-pyranones I [R = (Z)-MeC:CHMe, Bu, Ph], prepd. by iodolactonization of the corresponding 5-substituted (E)-2-bromo-2-en-4-ynoic acids (Z)-R1C≡CCH:CBrCO2H, were used as precursors to 5,6-disubstituted 3-methyl-2(2H)-pyranones II (R1 = Bu, R2 = 4-MeOC6H4; R1 = Ph, R2 = BuC≡C) (III) and 6-substituted 3-methyl-2(2H)-pyranones II [R1 = (Z)-, (E)-MeC:CHMe, Bu, R2 = H] (IV). The synthesis of compds. III involved two consecutive Stille-type reactions, whereas the approach followed to prep. compds. IV consisted of the selective redn. of the dihalogen derivs. I to the corresponding 6-substituted 3-bromo-2(2H)-pyranones, followed by a Pd/Cu-catalyzed reaction with tetramethyltin. However, this synthetic approach to compds. IV proved to be unsuitable for prepg. stereoisomerically pure fusalanipyrone II [R1 = (Z)-MeC:CHMe, R2 = H] (V), a natural product isolated from Fusarium solani. Nevertheless, V and gibepyrone A II [R1 = (E)-MeC:CHMe, R2 = H], which is a natural product isolated from Gibberella fujikuroi, could be synthesized in stereoisomerically pure form by reaction sequences involving iodolactonization of easily available (2Z,6Z)- and (2Z,6E)-2,6-dimethyl-2,6-octadien-4-ynoic acids, resp., followed by Pd-catalyzed triethylammonium formate redn. of the thus obtained 6-substituted 5-iodo-3-methyl-2(2H)-pyranones II [R1 = (Z)-MeC:CHMe, R2 = iodo; R1 = (E)-MeC:CHMe, R2 = iodo], resp
-
Selective synthesis of natural and unnatural 5,6-disubstituted 2(2H)-pyranones via iodolactonization of 5-substituted (Z)-2-en-4-ynoic acids
'Elsevier BV', 2001Co-Authors: Bellina Fabio, Biagetti M., Carpita Adriano, Rossi RenzoAbstract:Reaction of 5-substituted (Z)-2-en-4-ynoic acids with iodine and NaHCO3 in CH3CN or with ICl in CH2Cl2 affords mixts. of (E)-5-(1-iodoylidene)-2(5H)-furanones and 6-substituted 5-iodo-2(2H)-pyranones in which these last compds. are the major products. The 5-iodo-2(2H)-pyranones, which are easily sepd. chromatog. from the corresponding regioisomers, are able to undergo Stille-type reactions with a variety of organotin compds. to give 5,6-disubstituted 2(2H)-pyranones in moderate to good yields. One of these compds., i.e. 5-(1-butynyl)-2(2H)-pyranone, has been used as direct precursor to two substances produced by fungal culture LL-11G219, which function as androgen ligands, i.e. (Z)-5-(1-butenyl)-6-methyl-2(2H)-pyranone and 5-butyl-6-methyl-2(2H)-pyranone
Shugeng Cao - One of the best experts on this subject based on the ideXlab platform.
-
a new metabolite with a unique 4 pyranone γ lactam 1 4 thiazine moiety from a hawaiian plant associated fungus
Organic Letters, 2015Co-Authors: Yuanqing Ding, Bao-jun Yang, Gabriella Miklossy, Hong-quan Yin, James Turkson, Larry A Walker, Shugeng CaoAbstract:An endophytic fungus Paraphaeosphaeria neglecta FT462 isolated from the Hawaiian-plant Lycopodiella cernua (L.) Pic. Serm produced one unusual compound (1, paraphaeosphaeride A) with the 4-pyranone−γ-lactam–1,4-thiazine moiety, along with two new compounds (2 and 3, paraphaeosphaerides B and C, respectively) and the known compound (4). Compounds 1–3 were characterized by NMR and MS spectroscopic analysis. The absolute configuration of the 3-position of compound 1 was determined as S by electronic circular dichroism (ECD) calculations. Compound 3 also showed STAT3 inhibition at 10 μM.
-
A New Metabolite with a Unique 4‑Pyranone−γ-Lactam–1,4-Thiazine Moiety from a Hawaiian-Plant Associated Fungus
2015Co-Authors: Yuanqing Ding, Bao-jun Yang, Gabriella Miklossy, Hong-quan Yin, Larry A. Walker, James Turkson, Shugeng CaoAbstract:An endophytic fungus Paraphaeosphaeria neglecta FT462 isolated from the Hawaiian-plant Lycopodiella cernua (L.) Pic. Serm produced one unusual compound (1, paraphaeosphaeride A) with the 4-pyranone−γ-lactam–1,4-thiazine moiety, along with two new compounds (2 and 3, paraphaeosphaerides B and C, respectively) and the known compound (4). Compounds 1–3 were characterized by NMR and MS spectroscopic analysis. The absolute configuration of the 3-position of compound 1 was determined as S by electronic circular dichroism (ECD) calculations. Compound 3 also showed STAT3 inhibition at 10 μM
Renzo Rossi - One of the best experts on this subject based on the ideXlab platform.
-
New procedures for the selective synthesis of 2(2H)-pyranone derivatives and 3-aryl-4-iodoisocoumarins
Tetrahedron, 2002Co-Authors: Matteo Biagetti, Adriano Carpita, Paolo Stabile, Fabio Bellina, Renzo RossiAbstract:Abstract 5-Iodo-2(2 H )-pyranone derivatives have been selectively synthesized by reaction of stereodefined methyl 2-en-4-ynoates with iodine in MeCN, CH 2 Cl 2 or C 6 H 6 at 20°C (Method C) or by treatment of these esters with ICl in CH 2 Cl 2 at 20°C (Method B). Methods B and C proved also to be suitable for the preparation of 3-aryl-4-iodoisocoumarins from the corresponding methyl 2-(arylethynyl)benzoates. Interestingly, the high selectivity of iodolactonization of stereodefined methyl 2-en-4-ynoates by Method B allowed preparation in moderate yields of 2(2 H )-pyranone derivatives by a one-pot sequence of iodolactonization and Stille-type reactions.
-
Selective synthesis of 5,6-disubstituted 3-methyl-2(2H)-pyranones and 6-substituted 3-methyl-2(2H)-pyranones, including fusalanipyrone and gibepyrone A
'Wiley', 2002Co-Authors: Matteo Biagetti, Adriano Carpita, Fabio Bellina, Stéphane Viel, Luisa Mannina, Renzo RossiAbstract:The 6-substituted 3-bromo-5-iodo-2(2H)-pyranones, prepared by iodolactonization of the corresponding 5-substituted (E)-2-bromo-2-en-4-ynoic acids 10, were used as precursors to 5,6-disubstituted 3-methyl-2(2H)-pyranones and 6-substituted 3-methyl-2(2H)-pyranones . The synthesis of compounds involved two consecutive Stille-type reactions, whereas the approach followed to prepare compounds consisted of the selective reduction of the dihalogen derivatives to the corresponding 6-substituted 3-bromo-2(2H)-pyranones , followed by a Pd/Cu-catalysed reaction with tetramethyltin. However, this synthetic approach to compounds proved to be unsuitable for preparing stereoisomerically pure fusalanipyrone, a natural product isolated from Fusarium solani. Nevertheless, this compound which is a natural product isolated from Gibberella fujikuroi, could be synthesized in stereoisomerically pure form by reaction sequences involving iodolactonization of easily available (2Z,6Z)- and (2Z,6E)-2,6-dimethyl-2,6-octadien-4- ynoic acids, followed by Pd catalysed triethylammonium formate reduction of the thus obtained 6-substituted 5-iodo-3-methyl-2(2H)-pyranone
-
selective synthesis of natural and unnatural 5 6 disubstituted 2 2h pyranones via iodolactonization of 5 substituted z 2 en 4 ynoic acids
Tetrahedron, 2001Co-Authors: Fabio Bellina, Adriano Carpita, Matteo Biagetti, Renzo RossiAbstract:Abstract Reaction of 5-substituted ( Z )-2-en-4-ynoic acids with iodine and NaHCO 3 in CH 3 CN or with ICl in CH 2 Cl 2 affords mixtures of ( E )-5-(1-iodoylidene)-2(5 H )-furanones and 6-substituted 5-iodo-2(2 H )-pyranones in which these last compounds are the major products. The 5-iodo-2(2 H )-pyranones, which are easily separated chromatographically from the corresponding regioisomers, are able to undergo Stille-type reactions with a variety of organotin compounds to give 5,6-disubstituted 2(2 H )-pyranones in moderate to good yields. One of these compounds, i.e. 5-(1-butynyl)-2(2 H )-pyranone, has been used as direct precursor to two substances produced by fungal culture LL-11G219, which function as androgen ligands, i.e. ( Z )-5-(1-butenyl)-6-methyl-2(2 H )-pyranone and 5-butyl-6-methyl-2(2 H )-pyranone.
Yuanqing Ding - One of the best experts on this subject based on the ideXlab platform.
-
a new metabolite with a unique 4 pyranone γ lactam 1 4 thiazine moiety from a hawaiian plant associated fungus
Organic Letters, 2015Co-Authors: Yuanqing Ding, Bao-jun Yang, Gabriella Miklossy, Hong-quan Yin, James Turkson, Larry A Walker, Shugeng CaoAbstract:An endophytic fungus Paraphaeosphaeria neglecta FT462 isolated from the Hawaiian-plant Lycopodiella cernua (L.) Pic. Serm produced one unusual compound (1, paraphaeosphaeride A) with the 4-pyranone−γ-lactam–1,4-thiazine moiety, along with two new compounds (2 and 3, paraphaeosphaerides B and C, respectively) and the known compound (4). Compounds 1–3 were characterized by NMR and MS spectroscopic analysis. The absolute configuration of the 3-position of compound 1 was determined as S by electronic circular dichroism (ECD) calculations. Compound 3 also showed STAT3 inhibition at 10 μM.
-
A New Metabolite with a Unique 4‑Pyranone−γ-Lactam–1,4-Thiazine Moiety from a Hawaiian-Plant Associated Fungus
2015Co-Authors: Yuanqing Ding, Bao-jun Yang, Gabriella Miklossy, Hong-quan Yin, Larry A. Walker, James Turkson, Shugeng CaoAbstract:An endophytic fungus Paraphaeosphaeria neglecta FT462 isolated from the Hawaiian-plant Lycopodiella cernua (L.) Pic. Serm produced one unusual compound (1, paraphaeosphaeride A) with the 4-pyranone−γ-lactam–1,4-thiazine moiety, along with two new compounds (2 and 3, paraphaeosphaerides B and C, respectively) and the known compound (4). Compounds 1–3 were characterized by NMR and MS spectroscopic analysis. The absolute configuration of the 3-position of compound 1 was determined as S by electronic circular dichroism (ECD) calculations. Compound 3 also showed STAT3 inhibition at 10 μM
Bellina Fabio - One of the best experts on this subject based on the ideXlab platform.
-
An Economical Access to 3,4-Diaryl-2(5H)-furanones and 4-Aryl-6-methyl-2(2H)-pyranones via Pd-Catalyzed Suzuki-Type Arylation of 3-Aryl-4-tosyloxy-2(5H)-furanones and 6-Methyl-4-tosyloxy-2(2H)-pyranones, Respectively
'Wiley', 2009Co-Authors: Rossi Renzo, Bellina Fabio, Marchetti ChiaraAbstract:Both symmetrical and unsymmetrical 3,4-diaryl-substituted 2(5H)-furanones have been efficiently synthesized using an inexpensive procedure involving the Pd(OAc)2/PCy3-catalyzed Suzuki-type arylation of readily available 3-aryl-4-tosyloxy-2(5H)-furanones as the key step. The mild conditions of this arylation protocol have also been used for the high yielding synthesis of 4-aryl-6-methyl-2(2H)-pyranones from 6-methyl-4-tosyloxy-2(2H)-pyranone
-
6-Chloro-2(2H)-pyranone: a new 2(2H)-pyranone synthon
'Elsevier BV', 2003Co-Authors: Biagetti M., Bellina Fabio, Carpita Adriano, Rossi RenzoAbstract:6-Chloro-2(2H)-pyranone, which can be prepd. in high yield from com. available trans-glutaconic acid, undergoes facile Pd/Cu-catalyzed reaction with various 1-alkynes to give rise to the corresponding 6-(1-alkynyl)-2(2H)-pyranones in moderate to good yields. These last hitherto unknown compds. were used as direct precursors to 6-alkyl- and 6-[(Z)-1-alkenyl]-2(2H)-pyranones
-
Selective synthesis of 5,6-disubstituted 3-methyl-2(2H)-pyranones and 6-substituted 3-methyl-2(2H)-pyranones, including fusalanipyrone and gibepyrone A
'Wiley', 2002Co-Authors: Biagetti M., Bellina Fabio, Carpita Adriano, Viel S, Mannina L, Rossi RenzoAbstract:The 6-substituted 3-bromo-5-iodo-2(2H)-pyranones I [R = (Z)-MeC:CHMe, Bu, Ph], prepd. by iodolactonization of the corresponding 5-substituted (E)-2-bromo-2-en-4-ynoic acids (Z)-R1C≡CCH:CBrCO2H, were used as precursors to 5,6-disubstituted 3-methyl-2(2H)-pyranones II (R1 = Bu, R2 = 4-MeOC6H4; R1 = Ph, R2 = BuC≡C) (III) and 6-substituted 3-methyl-2(2H)-pyranones II [R1 = (Z)-, (E)-MeC:CHMe, Bu, R2 = H] (IV). The synthesis of compds. III involved two consecutive Stille-type reactions, whereas the approach followed to prep. compds. IV consisted of the selective redn. of the dihalogen derivs. I to the corresponding 6-substituted 3-bromo-2(2H)-pyranones, followed by a Pd/Cu-catalyzed reaction with tetramethyltin. However, this synthetic approach to compds. IV proved to be unsuitable for prepg. stereoisomerically pure fusalanipyrone II [R1 = (Z)-MeC:CHMe, R2 = H] (V), a natural product isolated from Fusarium solani. Nevertheless, V and gibepyrone A II [R1 = (E)-MeC:CHMe, R2 = H], which is a natural product isolated from Gibberella fujikuroi, could be synthesized in stereoisomerically pure form by reaction sequences involving iodolactonization of easily available (2Z,6Z)- and (2Z,6E)-2,6-dimethyl-2,6-octadien-4-ynoic acids, resp., followed by Pd-catalyzed triethylammonium formate redn. of the thus obtained 6-substituted 5-iodo-3-methyl-2(2H)-pyranones II [R1 = (Z)-MeC:CHMe, R2 = iodo; R1 = (E)-MeC:CHMe, R2 = iodo], resp
-
Selective synthesis of natural and unnatural 5,6-disubstituted 2(2H)-pyranones via iodolactonization of 5-substituted (Z)-2-en-4-ynoic acids
'Elsevier BV', 2001Co-Authors: Bellina Fabio, Biagetti M., Carpita Adriano, Rossi RenzoAbstract:Reaction of 5-substituted (Z)-2-en-4-ynoic acids with iodine and NaHCO3 in CH3CN or with ICl in CH2Cl2 affords mixts. of (E)-5-(1-iodoylidene)-2(5H)-furanones and 6-substituted 5-iodo-2(2H)-pyranones in which these last compds. are the major products. The 5-iodo-2(2H)-pyranones, which are easily sepd. chromatog. from the corresponding regioisomers, are able to undergo Stille-type reactions with a variety of organotin compds. to give 5,6-disubstituted 2(2H)-pyranones in moderate to good yields. One of these compds., i.e. 5-(1-butynyl)-2(2H)-pyranone, has been used as direct precursor to two substances produced by fungal culture LL-11G219, which function as androgen ligands, i.e. (Z)-5-(1-butenyl)-6-methyl-2(2H)-pyranone and 5-butyl-6-methyl-2(2H)-pyranone
