γ-Methyl-α-(alkylidene substituted)-γ-butyrolactones have been synthesized in two steps. The anio... more γ-Methyl-α-(alkylidene substituted)-γ-butyrolactones have been synthesized in two steps. The anion of allyl phosphonate 1 is condensed with different carbonyl compounds to afford α,βunsaturated esters 2a-g which are cyclised using 6N HCl to give title compounds.
γ-Methyl-α-(alkylidene substituted)-γ-butyrolactones have been synthesized in two steps. The anio... more γ-Methyl-α-(alkylidene substituted)-γ-butyrolactones have been synthesized in two steps. The anion of allyl phosphonate 1 is condensed with different carbonyl compounds to afford α,βunsaturated esters 2a-g which are cyclised using 6N HCl to give title compounds.
Cascade, 1 domino 2 or tandem 3 reactions play an important role in the construction of complex m... more Cascade, 1 domino 2 or tandem 3 reactions play an important role in the construction of complex molecular framework in fewer steps leading to saving time, cost and energy. In 2002, Schobert and Gordon reviewed domino Wittig and pericyclic reactions for bioactive heterocycles. 4a Taylor and Quesada reported a tandem Horner-Wadsworth-Emmons olefination/Claisen rearrangement/hydrolysis sequence. 4b In continuation of our interest in such reactions, we explored a Wittig reaction in combination with ene, 5a Diels-Alder, 5b electrocyclic, 5c oxidation 5d and reduction 5e reactions. Herein, we report one-pot synthesis of naturally occurring gravelliferone 1, balsamiferone 2 and 6,8-diprenylumbelliferone 3 from 2,4-diprenyloxybenzaldehyde 4, employing a cascade Wittig reaction, double Claisen & Cope rearrangements.
A short synthesis of (S)-pyrrolam A starting from readily available N-(benzyloxycarbonyl)-L-proli... more A short synthesis of (S)-pyrrolam A starting from readily available N-(benzyloxycarbonyl)-L-prolinol is described that makes use of a domino primary alcohol oxidation-Wittig reaction as the key step.
ABSTRACT A short synthesis of (S)-pyrrolam A starting from readily available N-(benzyloxycarbonyl... more ABSTRACT A short synthesis of (S)-pyrrolam A starting from readily available N-(benzyloxycarbonyl)-L prolinol is described that makes use of a domino primary alcohol oxidation-Witting reaction as the key step
1505-1508-Methyl- -(alkylidene substituted)--butyrolactones have been synthesized in two steps. T... more 1505-1508-Methyl- -(alkylidene substituted)--butyrolactones have been synthesized in two steps. The anion of allyl phosphonate 1 is condensed with different carbonyl compounds to afford ,-unsaturated esters 2a-gwhich are cyclised using 6N HCl to give title compounds
A short synthesis of (S)-pyrrolam A starting from readily available N-(benzyloxycarbonyl)-L proli... more A short synthesis of (S)-pyrrolam A starting from readily available N-(benzyloxycarbonyl)-L prolinol is described that makes use of a domino primary alcohol oxidation-Witting reaction as the key step
A short synthesis of (S)-pyrrolam A starting from readily available N-(benzyloxycarbonyl)-L-proli... more A short synthesis of (S)-pyrrolam A starting from readily available N-(benzyloxycarbonyl)-L-prolinol is described that makes use of a domino primary alcohol oxidation-Wittig reaction as the key step.
Domino oxidation of primary alcohols to a,b-unsaturated compounds using the combination of PCC-Na... more Domino oxidation of primary alcohols to a,b-unsaturated compounds using the combination of PCC-NaOAc and stabilized Wittig reagent and its application towards total synthesis of ABT-418 and 4-oxonon-2-enoic acid is described.
ChemInform Abstract Refluxing of the 3-aminothiophene (I) with 2-chloroethyl isocyanate (II) give... more ChemInform Abstract Refluxing of the 3-aminothiophene (I) with 2-chloroethyl isocyanate (II) gives the urea (III). Cyclization of (III) upon treatment with NaOH forms the heterocyclic compound (IV) mentioned in the title. Two alternative multi-step syntheses of (IV) are given in the original paper. Reaction of (IV) with nucleophiles such as (V) results in opening of the oxazole ring to give the products (VI). Desulfurization of (IV) produces the oxazolopyrimidine derivative (VII). Compound (IV) shows potent antigastric secretion activity.
Journal of Chemical Research-s - J CHEM RES-S, 2008
2-Carboxy-6-methoxybenzofuran-3-acetic acid anhydride is utilised for the synthesis of novel poly... more 2-Carboxy-6-methoxybenzofuran-3-acetic acid anhydride is utilised for the synthesis of novel polycyclic heteroaromatic compounds in which the benzofuran ring is fused or bound to pyrido[1,4]benzothiazine, thiazole, pyridine, pyrazolo-pyridine, pyrazole, pyrano-pyridine, and pyrazolo[1,5-a]pyrido[3,2-e]pyrimidines using versatile reaction strategies.
A cascade Wittig reaction-double Claisen & Cope rearrangements has been employed for a one-pot sy... more A cascade Wittig reaction-double Claisen & Cope rearrangements has been employed for a one-pot synthesis of diprenylated coumarins gravelliferone, balsamiferone & 6,8-diprenylumbelliferone from a common precursor 2,4-diprenyloxybenzaldehyde Cascade, 1 domino 2 or tandem 3 reactions play an important role in the construction of complex molecular framework in fewer steps leading to saving time, cost and energy. In 2002, Schobert and Gordon reviewed domino Wittig and pericyclic reactions for bioactive heterocycles. 4a Taylor and Quesada reported a tandem Horner-Wadsworth-Emmons olefination/Claisen rearrangement/hydrolysis sequence. 4b In continuation of our interest in such reactions, we explored a Wittig reaction in combination with ene, 5a Diels-Alder, 5b electrocyclic, 5c oxidation 5d and reduction 5e reactions. Herein, we report one-pot synthesis of naturally occurring gravelliferone 1, balsamiferone 2 and 6,8-diprenylumbelliferone 3 from 2,4-diprenyloxybenzaldehyde 4, employing a cascade Wittig reaction, double Claisen & Cope rearrangements.
A short synthesis of (S)-Pyrrolam A starting from readily available Nbenzyloxycarbonyl-L-prolinol... more A short synthesis of (S)-Pyrrolam A starting from readily available Nbenzyloxycarbonyl-L-prolinol is described making use of a domino primary alcohol oxidation Wittig reaction as a key step.
γ-Methyl-α-(alkylidene substituted)-γ-butyrolactones have been synthesized in two steps. The anio... more γ-Methyl-α-(alkylidene substituted)-γ-butyrolactones have been synthesized in two steps. The anion of allyl phosphonate 1 is condensed with different carbonyl compounds to afford α,βunsaturated esters 2a-g which are cyclised using 6N HCl to give title compounds.
γ-Methyl-α-(alkylidene substituted)-γ-butyrolactones have been synthesized in two steps. The anio... more γ-Methyl-α-(alkylidene substituted)-γ-butyrolactones have been synthesized in two steps. The anion of allyl phosphonate 1 is condensed with different carbonyl compounds to afford α,βunsaturated esters 2a-g which are cyclised using 6N HCl to give title compounds.
Cascade, 1 domino 2 or tandem 3 reactions play an important role in the construction of complex m... more Cascade, 1 domino 2 or tandem 3 reactions play an important role in the construction of complex molecular framework in fewer steps leading to saving time, cost and energy. In 2002, Schobert and Gordon reviewed domino Wittig and pericyclic reactions for bioactive heterocycles. 4a Taylor and Quesada reported a tandem Horner-Wadsworth-Emmons olefination/Claisen rearrangement/hydrolysis sequence. 4b In continuation of our interest in such reactions, we explored a Wittig reaction in combination with ene, 5a Diels-Alder, 5b electrocyclic, 5c oxidation 5d and reduction 5e reactions. Herein, we report one-pot synthesis of naturally occurring gravelliferone 1, balsamiferone 2 and 6,8-diprenylumbelliferone 3 from 2,4-diprenyloxybenzaldehyde 4, employing a cascade Wittig reaction, double Claisen & Cope rearrangements.
A short synthesis of (S)-pyrrolam A starting from readily available N-(benzyloxycarbonyl)-L-proli... more A short synthesis of (S)-pyrrolam A starting from readily available N-(benzyloxycarbonyl)-L-prolinol is described that makes use of a domino primary alcohol oxidation-Wittig reaction as the key step.
ABSTRACT A short synthesis of (S)-pyrrolam A starting from readily available N-(benzyloxycarbonyl... more ABSTRACT A short synthesis of (S)-pyrrolam A starting from readily available N-(benzyloxycarbonyl)-L prolinol is described that makes use of a domino primary alcohol oxidation-Witting reaction as the key step
1505-1508-Methyl- -(alkylidene substituted)--butyrolactones have been synthesized in two steps. T... more 1505-1508-Methyl- -(alkylidene substituted)--butyrolactones have been synthesized in two steps. The anion of allyl phosphonate 1 is condensed with different carbonyl compounds to afford ,-unsaturated esters 2a-gwhich are cyclised using 6N HCl to give title compounds
A short synthesis of (S)-pyrrolam A starting from readily available N-(benzyloxycarbonyl)-L proli... more A short synthesis of (S)-pyrrolam A starting from readily available N-(benzyloxycarbonyl)-L prolinol is described that makes use of a domino primary alcohol oxidation-Witting reaction as the key step
A short synthesis of (S)-pyrrolam A starting from readily available N-(benzyloxycarbonyl)-L-proli... more A short synthesis of (S)-pyrrolam A starting from readily available N-(benzyloxycarbonyl)-L-prolinol is described that makes use of a domino primary alcohol oxidation-Wittig reaction as the key step.
Domino oxidation of primary alcohols to a,b-unsaturated compounds using the combination of PCC-Na... more Domino oxidation of primary alcohols to a,b-unsaturated compounds using the combination of PCC-NaOAc and stabilized Wittig reagent and its application towards total synthesis of ABT-418 and 4-oxonon-2-enoic acid is described.
ChemInform Abstract Refluxing of the 3-aminothiophene (I) with 2-chloroethyl isocyanate (II) give... more ChemInform Abstract Refluxing of the 3-aminothiophene (I) with 2-chloroethyl isocyanate (II) gives the urea (III). Cyclization of (III) upon treatment with NaOH forms the heterocyclic compound (IV) mentioned in the title. Two alternative multi-step syntheses of (IV) are given in the original paper. Reaction of (IV) with nucleophiles such as (V) results in opening of the oxazole ring to give the products (VI). Desulfurization of (IV) produces the oxazolopyrimidine derivative (VII). Compound (IV) shows potent antigastric secretion activity.
Journal of Chemical Research-s - J CHEM RES-S, 2008
2-Carboxy-6-methoxybenzofuran-3-acetic acid anhydride is utilised for the synthesis of novel poly... more 2-Carboxy-6-methoxybenzofuran-3-acetic acid anhydride is utilised for the synthesis of novel polycyclic heteroaromatic compounds in which the benzofuran ring is fused or bound to pyrido[1,4]benzothiazine, thiazole, pyridine, pyrazolo-pyridine, pyrazole, pyrano-pyridine, and pyrazolo[1,5-a]pyrido[3,2-e]pyrimidines using versatile reaction strategies.
A cascade Wittig reaction-double Claisen & Cope rearrangements has been employed for a one-pot sy... more A cascade Wittig reaction-double Claisen & Cope rearrangements has been employed for a one-pot synthesis of diprenylated coumarins gravelliferone, balsamiferone & 6,8-diprenylumbelliferone from a common precursor 2,4-diprenyloxybenzaldehyde Cascade, 1 domino 2 or tandem 3 reactions play an important role in the construction of complex molecular framework in fewer steps leading to saving time, cost and energy. In 2002, Schobert and Gordon reviewed domino Wittig and pericyclic reactions for bioactive heterocycles. 4a Taylor and Quesada reported a tandem Horner-Wadsworth-Emmons olefination/Claisen rearrangement/hydrolysis sequence. 4b In continuation of our interest in such reactions, we explored a Wittig reaction in combination with ene, 5a Diels-Alder, 5b electrocyclic, 5c oxidation 5d and reduction 5e reactions. Herein, we report one-pot synthesis of naturally occurring gravelliferone 1, balsamiferone 2 and 6,8-diprenylumbelliferone 3 from 2,4-diprenyloxybenzaldehyde 4, employing a cascade Wittig reaction, double Claisen & Cope rearrangements.
A short synthesis of (S)-Pyrrolam A starting from readily available Nbenzyloxycarbonyl-L-prolinol... more A short synthesis of (S)-Pyrrolam A starting from readily available Nbenzyloxycarbonyl-L-prolinol is described making use of a domino primary alcohol oxidation Wittig reaction as a key step.
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