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.
Graphical Abstract
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