Synthesis of Carbocyclic Nucleosides, (-)-Neplanocin A and Its Analogues

Junzo Nokami; Hiroyuki Matsuura; Hideki Takahashi; Manabu Yamashita

doi:10.1055/s-1994-22900

Synlett 1994; 1994(7): 491-493
DOI: 10.1055/s-1994-22900

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Synthesis of Carbocyclic Nucleosides, (-)-Neplanocin A and Its Analogues

Junzo Nokami^* , Hiroyuki Matsuura, Hideki Takahashi, Manabu Yamashita

^*Department of Applied Chemistry, Okayama University of Science, Ridai, Okayama 700, Japan

Abstract

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The title compounds, 9-[(1′R,2′S,3′R)-4′-hydroxymethyl -cyclopent-4′-en-1′-yl)purines, were synthesized via chemoselective S_N2 substitution (by the Mitsunobu reaction) of the sec-allylic hydroxy group of a protected carbofuranose synthon for purines at the N-9 position. The carbofuranose synthon, (3S,4S,8R)-1-benzyloxymethyl-3-hydroxy-6,6-dimethyl-5,7-dioxabicyclo[3.3.0]oct-1-ene, was prepared from (4S,8S)-6,6-dimethyl-5,7-dioxabicyclo[3.3.0]act-2-en-1-one via stereospecific chloromethylation of the carbonyl group followed by five step conversion.

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