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Enantiomerically pure chiral building blocks for syntheses of carbocyclic nucleoside analogues: A formal synthesis of aristeromycin

✍ Scribed by Helmchen, Günter ;Krotz, Achim ;Neumann, Hans-Peter ;Ziegler, Manfred L.

Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
521 KB
Volume
1993
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

(+)‐(1__R__,4__R__)‐Bicyclo[2.2.1]hept‐5‐en‐2‐one (7) was prepared in 78.5% yield by oxidative degradation of (+)‐(1__R__)‐endo‐bicyclo[2.2.1]hept‐5‐ene‐2‐carboxylic acid (4) by using an improved procedure for the oxidation of the dianion of 4 with dioxygen. Dihydroxylation of 7 with osmium tetroxide furnished the cis exo addition product 8c and, via reversible retro aldol reaction, the trans isomer 8t which was characterized by X‐ray crystal structure analysis. 8c was transformed in four reaction steps into the lactone 2 which is a known starting material for a synthesis of the antiviral antibiotic aristeromycin (1). 8t is a potential starting material for syntheses of carbocyclic analogues of arabinofuranosyl nucleotides, e.g., the antiviral agent cyclaradine (3).

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