First enantioselective synthesis of (−)-neplanocin F

Rodríguez, Sergio; Edmont, Dolorès; Mathé, Christophe; Philouze, Christian

doi:10.1016/j.tet.2007.04.094

Cited by 9 publications

(2 citation statements)

References 28 publications

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“…(-)-Neplanocin C ( 394) and (-)-neplanocin F (395) have also been isolated from the same fungus. Mathe ánd co-workers reported that coupling of the precursor alcohol with 6-chloropurine (instead of adenine itself) gave low isolated yields of the intermediate alkylated product required for the synthesis of (-)-neplanocin F. 1152 Synthesis of (-)-neplanocin A and many analogues was reported earlier by Chu and co-workers, using suitably protected/masked purine/pyrimidine bases. 1153 Several other publications on the synthesis of neplanocin A and C analogues wherein a Mitsunobu protocol is used are also available.…”

Section: N-alkylation Of Nucleobases Including 6-chloropurinementioning

confidence: 86%

Mitsunobu and Related Reactions: Advances and Applications

et al. 2009

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His research interests include Organophosphorus Chemistry and Main Group Chemistry. He has over 115 publications so far and is a fellow of the Indian Academy of Sciences, Bangalore. N. N. Bhuvan Kumar was born in Cherukupalli, Guntur, India. After completing his B.Sc. from Nagarjuna University, he joined the School of Chemistry, University of Hyderabad, as a postgraduate student in the year 2000 and obtained his Master's degree in Chemistry. Currently, he is pursuing a Ph.D. on Organophosphonates under the supervision of Prof. K. C. Kumara Swamy. E. Balaraman was born in Kancheepuram, Chennai, India, in 1980. He received his M.Sc. in Chemistry from Vivekananda College [Madras University (2002)] and his Ph.D. degree in the areas of organophosphonates and modified BINOLs under the guidance of Prof. K. C. Kumara Swamy. Presently he is a postdoctoral fellow with Professors David Milstein and Ronny Neumann at the Weizmann Institute of Science, Israel. K. V. P. Pavan Kumar was born in Hyderabad (Andhra Pradesh), India, in 1979. He obtained his B.Sc. (Chemistry Honors) and M.Sc. (Chemistry) degrees from Sri Sathya Sai Institute of Higher Learning, Puttaparthi, A.P., India. He obtained his Ph.D. degree under the guidance of Prof. K. C. Kumara Swamy in October 2006. Presently he is working as a postdoctoral fellow in the area of hydroamination reactions using new titanium catalysts with Prof. Pierre Le Gendre at the Universite ´de Bourgogne, France.

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Section: N-alkylation Of Nucleobases Including 6-chloropurinementioning

confidence: 86%

Mitsunobu and Related Reactions: Advances and Applications

et al. 2009

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“…Compound (+/−)- 21 was obtained as sodium salt after reversed phase column chromatography and ion exchange chromatography and its structural assignments were based upon 1 H and 13 C NMR spectra and correlation experiments. It is noteworthy that the carbocyclic methylphosphonates (+/−)- 16 and (+/−)- 21 have structural similarity with carbonucleosides belonging to the neplanocin family, in particular, with neplanocin F [ 13 ].…”

Section: Resultsmentioning

confidence: 99%

Revaluation of biomass-derived furfuryl alcohol derivatives for the synthesis of carbocyclic nucleoside phosphonate analogues

Mohamed¹,

Philouze²,

Mathé³

2017

Beilstein J. Org. Chem.

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The racemic synthesis of new carbocyclic nucleoside methylphosphonate analogues bearing purine bases (adenine and guanine) was accomplished using bio-sourced furfuryl alcohol derivatives. All compounds were prepared using a Mitsunobu coupling between the heterocyclic base and an appropriate carbocyclic precursor. After deprotection, the compounds were evaluated for their activity against a large number of viruses. However, none of them showed significant antiviral activity or cytotoxicity.

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