Vasudeva Naidu Sagi
Research interests
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InterestsOrganic Synthesis, Natural Product Synthesis, Asymmetric Synthesis, Synthetic Organic Chemistry/Medicinal Chemistry, novel methodology development, CNS drug discovery, Prebiotic chemistry, hit-to-lead optimization, peptides synthesis, oligonucleotide synthesis
Publications
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8.58Impact points
Exploratory experiments on the chemistry of the "glyoxylate scenario": formation of ketosugars from dihydroxyfumarate.
Journal of the American Chemical Society. 02/2012; 134(7):3577-89.
In the context of a "glyoxylate scenario" of primordial metabolism, (1) the reactions of dihydroxyfumarate (DHF) with reactive small molecule aldehydes (e.g., glyoxylate, formaldehyde, glycolaldehyde, and glyceraldehyde) in water were investigated and shown to form dihydroxyacetone, tetrul... [more] In the context of a "glyoxylate scenario" of primordial metabolism, (1) the reactions of dihydroxyfumarate (DHF) with reactive small molecule aldehydes (e.g., glyoxylate, formaldehyde, glycolaldehyde, and glyceraldehyde) in water were investigated and shown to form dihydroxyacetone, tetrulose, and the two pentuloses, with almost quantitative conversion. The practically clean and selective formation of ketoses in these reactions, with no detectable admixture of aldoses, stands in stark contrast to the formose reaction, where a complex mixture of linear and branched aldoses and ketoses are produced. These results suggest that the reaction of DHF with aldehydes could constitute a reasonable pathway for the formation of carbohydrates and allow for alternative potential prebiotic scenarios to the formose reaction to be considered.
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2.65Impact points
Synthesis and biological evaluation of novel pyrimidine derivatives as sub-micromolar affinity ligands of GalR2.
Bioorganic & medicinal chemistry letters. 12/2011; 21(23):7210-5.
GalR1 and GalR2 represent unique pharmacological targets for treatment of seizures and epilepsy. A novel series of 2,4,6-triaminopyrimidine derivatives were synthesized and found to have sub-micromolar affinity for GalR2. Optimization of a series of 2,4,6-triaminopyrimidines led to the discovery of ... [more] GalR1 and GalR2 represent unique pharmacological targets for treatment of seizures and epilepsy. A novel series of 2,4,6-triaminopyrimidine derivatives were synthesized and found to have sub-micromolar affinity for GalR2. Optimization of a series of 2,4,6-triaminopyrimidines led to the discovery of several analogs with IC50 values ranging from 0.3 to 1 μM.
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11.83Impact points
Diastereoselective Self-Condensation of Dihydroxyfumaric Acid in Water: Potential Route to Sugars.
Angewandte Chemie (International ed. in English). 07/2011;
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3.10Impact points
Enantio- and Diastereocontrolled Total Synthesis of (+)-Strictifolione
European Journal of Organic Chemistry. 01/2010;
A concise and practical enantioselective synthesis of (+)- strictifolione has been achieved in high diastereomeric excess using Jacobsen’s hydrolytic kinetic resolution, proline-catalyzed sequential α-aminoxylation and Horner–Wadsworth– Emmons olefination of aldehyde and cross olefin/ringclosing met... [more] A concise and practical enantioselective synthesis of (+)- strictifolione has been achieved in high diastereomeric excess using Jacobsen’s hydrolytic kinetic resolution, proline-catalyzed sequential α-aminoxylation and Horner–Wadsworth– Emmons olefination of aldehyde and cross olefin/ringclosing metathesis as the key steps.
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3.22Impact points
Enantioselective syntheses of (-)-pinellic acid, alpha- and beta-dimorphecolic acid
Tetrahedron. 01/2007; 63:7624–7633.
Abstract—An efficient enantioselective convergent approach for the synthesis of (-)-pinellic acid 1, alpha- and beta-dimorphecolic acid (2 and 3) from 1,9-nonane diol is described. The synthetic strategy features Sharpless asymmetric hydroxylation, Sonogashira coupling and Birch reduction.... [more] Abstract—An efficient enantioselective convergent approach for the synthesis of (-)-pinellic acid 1, alpha- and beta-dimorphecolic acid (2 and 3) from 1,9-nonane diol is described. The synthetic strategy features Sharpless asymmetric hydroxylation, Sonogashira coupling and Birch reduction.
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2.66Impact points
Enantioselective synthesis of (-)-pinellic acid
Tetrahedron Letters. 01/2007; 48:2279–2282.
An enantioselective convergent approach toward the total synthesis of pinellic acid 1 from 1,9-nonanediol is described. The synthetic strategy features iterative Sharpless asymmetric dihydroxylation, Sonogashira coupling and Birch reduction.... [more] An enantioselective convergent approach toward the total synthesis of pinellic acid 1 from 1,9-nonanediol is described. The synthetic strategy features iterative Sharpless asymmetric dihydroxylation, Sonogashira coupling and Birch reduction.
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2.66Impact points
A simple and efficient approach to 1,3-aminoalcohols: application to the synthesis of (+)-negamycin
Tetrahedron Letters. 01/2007;
A short and practical enantioselective synthesis of (+)-negamycin has been achieved in high enantio- and diastereomeric excess using an iterative Jacobsen’s hydrolytic kinetic resolution as the key step.... [more] A short and practical enantioselective synthesis of (+)-negamycin has been achieved in high enantio- and diastereomeric excess using an iterative Jacobsen’s hydrolytic kinetic resolution as the key step.
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3.22Impact points
Application of hydrolytic kinetic resolution (HKR) in the synthesis of bioactive compounds
Tetrahedron. 01/2007; 63:2745–2785.
Hydrolytic kinetic resolution (HKR) developed by Jacobsen has emerged in recent times as a powerful tool to synthesize both terminal epoxides and their corresponding diols in highly enantiomerically pure form. In this review we have covered the application of HKR method for the first time in the syn... [more] Hydrolytic kinetic resolution (HKR) developed by Jacobsen has emerged in recent times as a powerful tool to synthesize both terminal epoxides and their corresponding diols in highly enantiomerically pure form. In this review we have covered the application of HKR method for the first time in the synthesis of biologically active compounds.
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4.22Impact points
Enantio- and diastereocontrolled total synthesis of (+)-boronolide.
The Journal of organic chemistry. 06/2006; 71(10):3935-41.
An efficient stereoselective total synthesis of (+)-boronolide from valeraldehyde is described. The key steps include a Sharpless asymmetric hydroxylation, a chelation-controlled vinyl Grignard reaction followed by a Sharpless asymmetric epoxidation, hydrolytic kinetic resolution, and a ring-closing... [more] An efficient stereoselective total synthesis of (+)-boronolide from valeraldehyde is described. The key steps include a Sharpless asymmetric hydroxylation, a chelation-controlled vinyl Grignard reaction followed by a Sharpless asymmetric epoxidation, hydrolytic kinetic resolution, and a ring-closing metathesis.
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5.38Impact points
A simple and efficient approach to 1,3-polyols: application to the synthesis of cryptocarya diacetate.
Chemistry (Weinheim an der Bergstrasse, Germany). 03/2006; 12(5):1397-402.
A highly enantio- and stereoselective synthetic strategy for both syn- and anti-1,3-polyols has been developed. The sequence involves iterative Jacobsen's hydrolytic kinetic resolution (HKR), diastereoselective iodine-induced electrophilic cyclization, and ring-closing metathesis (RCM). This pro... [more] A highly enantio- and stereoselective synthetic strategy for both syn- and anti-1,3-polyols has been developed. The sequence involves iterative Jacobsen's hydrolytic kinetic resolution (HKR), diastereoselective iodine-induced electrophilic cyclization, and ring-closing metathesis (RCM). This protocol has subsequently been utilized for the synthesis of cryptocarya diacetate, a natural product with broad range of biological activity.
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A simple and efficient approach to 1,3-Polyols: Application to the syntheses of tarchonanthuslactone, cryptocarya diacetate and (+)-strictifolione
American Chemical Society - Council of Scientific and Industrial research (ACS-CSIR),, National Chemical laboratory, Pune, India; 01/2006
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4.22Impact points
Total synthesis of microcarpalide.
The Journal of organic chemistry. 06/2005; 70(10):4207-10.
[reaction: see text] An efficient, convergent approach for the total synthesis of microcarpalide (1) is described. The synthetic strategy features the Sharpless asymmetric dihydroxylation, regioselective epoxide opening with various nucleophiles such as a lithium acetylide and cuprates derived from ... [more] [reaction: see text] An efficient, convergent approach for the total synthesis of microcarpalide (1) is described. The synthetic strategy features the Sharpless asymmetric dihydroxylation, regioselective epoxide opening with various nucleophiles such as a lithium acetylide and cuprates derived from the vinyl stannane and the vinyl iodide for the construction of a C7-C8 trans-double bond and Yamaguchi macrolactonization as the key steps.
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4.22Impact points
Efficient total synthesis of sapinofuranone B.
The Journal of organic chemistry. 05/2005; 70(7):2843-6.
[structure: see text] An efficient enantioselective synthesis of sapinofuranone B (1) using Sharpless asymmetric dihydroxylation, Sonogashira coupling, and Wittig olefination as the key steps is described.... [more] [structure: see text] An efficient enantioselective synthesis of sapinofuranone B (1) using Sharpless asymmetric dihydroxylation, Sonogashira coupling, and Wittig olefination as the key steps is described.
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2.66Impact points
Enantioselective synthesis of tarchonanthuslactone via iterative hydrolytic kinetic resolution
Tetrahedron Letters. 01/2005; 46:6571–6573.
A short and practical enantioselective synthesis of tarchonanthuslactone has been achieved in high diastereomeric excess using iterative Jacobsen's hydrolytic kinetic resolution and ring closing metathesis as the key steps.... [more] A short and practical enantioselective synthesis of tarchonanthuslactone has been achieved in high diastereomeric excess using iterative Jacobsen's hydrolytic kinetic resolution and ring closing metathesis as the key steps.
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2.66Impact points
Stereoselective synthesis of (+)-boronolide
Tetrahedron Letters. 01/2005; 46:2129–2131.
Abstract—An efficient enantio- and stereocontrolled total synthesis of (+)-boronolide from valeraldehyde is described. The key steps include a Sharpless asymmetric dihydroxylation, a chelation controlled Grignard reaction followed by Sharpless asymmetric epoxidation and a ring closing metathesis.... [more] Abstract—An efficient enantio- and stereocontrolled total synthesis of (+)-boronolide from valeraldehyde is described. The key steps include a Sharpless asymmetric dihydroxylation, a chelation controlled Grignard reaction followed by Sharpless asymmetric epoxidation and a ring closing metathesis.
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2.66Impact points
An efficient total synthesis of sulfobacin A
Tetrahedron Letters. 01/2004; 45:9641–9643.
A short and efficient enantioselective synthesis of sulfobacin A has been achieved using the Sharpless asymmetric dihydroxylation and the regiospecific nucleophilic opening of a cyclic sulfate as the key steps.... [more] A short and efficient enantioselective synthesis of sulfobacin A has been achieved using the Sharpless asymmetric dihydroxylation and the regiospecific nucleophilic opening of a cyclic sulfate as the key steps.
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Enantioselective total synthesis of microcarpalide
6th National Symposium in Chemistry, Indian Institute of Technology, Kanpur, India; 01/2004
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2.66Impact points
A practical enantioselective synthesis of massoialactone via hydrolytic kinetic resolution
Tetrahedron Letters. 01/2004; 45:849–851.
An efficient enantioselective synthesis of (R)- and (S)-massoialactone has been achieved. The key steps are the hydrolytic kinetic resolution of a racemic epoxyheptane with (R,R)-(salen)–CoIIIOAc complex and ring-closing metathesis of homoallylic alcohol derived acrylate esters using Grubb�s catalys... [more] An efficient enantioselective synthesis of (R)- and (S)-massoialactone has been achieved. The key steps are the hydrolytic kinetic resolution of a racemic epoxyheptane with (R,R)-(salen)–CoIIIOAc complex and ring-closing metathesis of homoallylic alcohol derived acrylate esters using Grubb�s catalyst.
Following (9)
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Jerome Baker
Sigma Xi, The Scientific Research Society -
Prakash Sambavekar
Shivaji University, Kolhapur -
Uwe Klein
Theravance, Inc. -
Naresh Veesam
RA CHEM PHARMA LTD -
Pawan Tambade
Institute of Chemical Technology
Topics (2)
