Research Topics | Kavirayani R PrasadSummaryCountry: India Publications
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Enantioselective formal synthesis of palmerolide AKavirayani R Prasad
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India
Org Lett 13:4252-5. 2011..Key strategies in the synthesis include the oxidative furan ring-opening of a chiral furyl carbinol for the installation of the 1,4-dienol core and a Jung nonaldol-aldol reaction for the dienamide core...
Enantiodivergent synthesis of both enantiomers of gypsy moth pheromone disparlureKavirayani R Prasad
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India
J Org Chem 72:3155-7. 2007..Enantiodivergent synthesis of both (-)- and (+)-disparlure, a bioactive pheromone, possessing a cis-epoxide has been accomplished. The key step involves the cross metathesis of a chiral homoallylic alcohol derived from l-(+)-tartaric acid...- Total synthesis of (-)-anamarineKavirayani R Prasad
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India
J Org Chem 76:6889-93. 2011..The main feature of the synthesis is the utility of hitherto unexplored β-keto phosphonate derived from tartaric acid amide and further elaboration involving stereoselective reduction... - Enantioselective synthesis of possible diastereomers of heptadeca-1-ene-4,6-diyne-3,8,9,10-tetrol; putative structure of a conjugated diyne natural product isolated from Hydrocotyle leucocephalaKavirayani R Prasad
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India
J Org Chem 76:2029-39. 2011..The reported spectral data of the natural product did not match those of any of the isomers that were synthesized and established that the structure proposed for the natural product is not correct and requires revision... - Stereoselective total synthesis of (+)-cardiobutanolideKavirayani R Prasad
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India
J Org Chem 73:2916-9. 2008..Key features of the synthesis include the elaboration of a gamma-hydroxy butyramide obtained from the dimethylamide of tartaric acid, involving a combination of the addition of 1,3-dithian-2-yllithium and stereoselective reduction... - Stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine [jaspine B]Kavirayani R Prasad
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India
J Org Chem 72:6312-5. 2007..The synthetic route is operationally simple, diastereoselective and is amenable for the synthesis of a number of analogues of pachastrissamine... - Stereoselective synthesis of (+)-goniothalesdiolKavirayani R Prasad
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India
J Org Chem 71:3643-5. 2006..Key features include an FeCl3 mediated THF formation with very high selectivity. Synthesis of natural gonithalesdiol and its analogue 2,5-bis-epi-goniothalesdiol was achieved from a common intermediate... - Stereoselective total synthesis of bioactive styryllactones (+)-goniofufurone, (+)7-epi-goniofufurone, (+)-goniopypyrone, (+)-goniotriol, (+)-altholactone, and (-)-etharvensinKavirayani R Prasad
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India
J Org Chem 73:2-11. 2008.... - Formal total synthesis of palmerolide AAmit B Pawar
Department of Organic Chemistry, Indian Institute of Science, Sir C V Raman Av, Bangalore 560 012, India
Chemistry 18:15202-6. 2012.... - Asymmetric synthesis of polyhydroxy alpha-amino acids with the sulfinimine-mediated asymmetric strecker reaction: 2-amino 2-deoxy L-xylono-1,5-lactone (polyoxamic acid lactone)Franklin A Davis
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122 2585, USA
J Org Chem 67:7802-6. 2002..A double stereodifferentiation effect was not observed and the diastereoselectivity is controlled by the absolute configuration of the sulfinyl group. Hydrolysis of the amino nitriles afforded the lactone rather than polyoxamic acid... - Asymmetric synthesis of beta-amino carbonyl compounds with N-sulfinyl beta-amino Weinreb amidesFranklin A Davis
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA
J Org Chem 70:2184-90. 2005..N-Sulfinyl beta-amino Weinreb amides are prepared by reaction of the potassium enolate of N-methoxy N-methylacetamide with sulfinimines (N-sulfinyl imines) or lithium N,O-dimethylhydroxylamine with N-sulfinyl beta-amino esters... - Sulfinimine-mediated asymmetric synthesis of beta-hydroxy alpha-amino phosphonatesFranklin A Davis
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA
J Org Chem 68:7249-53. 2003..The addition of potassium dialkyl phosphites to enantiopure O-protected alpha-hydroxy sulfinimine pseudoenantiomers affords beta-hydroxy alpha-amino phosphonates in good yield and de. The reaction exhibits a strong match-mismatch effect... - Asymmetric synthesis of aziridine 2-phosphonates from enantiopure sulfinimines (N-sulfinyl imines). Synthesis of alpha-amino phosphonatesFranklin A Davis
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA
J Org Chem 68:2410-9. 2003..Using transfer hydrogenation conditions, the NH-aziridines were regioselectively opened to the corresponding enantiopure alpha-amino phosphonates without N-activation and in excellent yield... - N-sulfinyl beta-amino Weinreb amides: synthesis of enantiopure beta-amino carbonyl compounds. Asymmetric synthesis of (+)-sedridine and (-)-allosedridineFranklin A Davis
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA
Org Lett 5:925-7. 2003..These new chiral building blocks are useful for the asymmetric synthesis of beta-amino carbonyl compounds, as illustrated here by the concise enantioselective syntheses of sedum alkaloids (+)-sedridine and (-)-allosedridine... - 2H-Azirine 3-phosphonates: a new class of chiral iminodienophiles. Asymmetric synthesis of quaternary piperidine phosphonatesFranklin A Davis
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA
Org Lett 4:655-8. 2002....