ISSN:
0170-2041
Keywords:
Antiviral agents
;
Aristeromycin
;
Cyclaradine
;
(+)-(1R,4R)-5-Norbornen-2-one
;
2-Norbornanones, 5,6-dihydroxy-
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
(+)-(1R,4R)-Bicyclo[2.2.1]hept-5-en-2-one (7) was prepared in 78.5% yield by oxidative degradation of (+)-(1R)-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).
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1993199301213
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