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KMID : 0617319970060010179
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Journal of Pharmacetical Sceiences Ewha Womans University
1997 Volume.6 No. 1 p.179 ~ p.182
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Use of a Cyclic Sulfite as an Epoxide Surrogate in the Regioselective Synthesis of a Carbocyclic Ring-Enlarged 4´,1´a-Methano Oxetanocin Analogue
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Jeong Lak-S.
Victor E. Marquez
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Abstract
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Although cyclic sulfites are less reactive than their cyclic sulfate counterparts, the present work shows that cyclic sulfite 15a is a useful synthon for the convergent synthesis of carbocyclic nucleosides. Target compound 6, which represents a rigid carbocyclic nucleoside mimic of anti-HIV active 9-〔2´,3´-dideoxy-3´-C-(hydroxymethyl)-β-erythro-pentofuranosyl〕adenine (3), was obtained after regioselective ring opening of 15a with adenine and radical-induced deoxygenation of the extra hydroxyl group.
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KEYWORD
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