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Synthesis of Carbocyclic Nucleosides (+)-Neplanocin A, (+)-Aristeromycin and 4'-epi-(+)-Aristeromycin from D-Fructose

[ Vol. 16 , Issue. 9 ]

Author(s):

Perali Ramu Sridhar*, Vennam Dinesh Kumar Reddy, Mandava Suresh, Nadiveedhi Maheshwara Reddy and K. Shiva Kumar   Pages 750 - 758 ( 9 )

Abstract:


D-Fructose is used as the chiral pool starting material for the stereoselective total synthesis of (+)-neplanocin A. Zinc mediated fragmentation, ring-closing metathesis and oxidative rearrangement of cyclic tertiary allylic alcohol are used as the key steps in achieving the synthesis of key carbocylic intermediate. Further, stereoselective total synthesis of 4'-epi-(+)-aristeromycin and the conversion of (+)-neplanocin A to a mixture of (+)-aristeromycin and 4'-epi-(+)-aristeromycin are described.

Keywords:

Carbocycles, nucleosides, total synthesis, natural products, D-Fructose, metathesis.

Affiliation:

School of Chemistry, University of Hyderabad, C. R. Rao Road, Hyderabad-500 046, Department of Chemistry, GITAM University, Hyderabad Campus, Hyderabad – 502329, School of Chemistry, University of Hyderabad, C. R. Rao Road, Hyderabad-500 046, School of Chemistry, University of Hyderabad, C. R. Rao Road, Hyderabad-500 046, Department of Chemistry, GITAM University, Hyderabad Campus, Hyderabad – 502329



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