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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

Title
Use of a cyclic sulfite as an epoxide surrogate in the regioselective synthesis of a carbocyclic ring-enlarged 4′,1'a-methano oxetanocin analogue
Authors
Jeong L.S.Marquez V.E.
Ewha Authors
정낙신
Issue Date
1996
Journal Title
Tetrahedron Letters
ISSN
0040-4039JCR Link
Citation
vol. 37, no. 14, pp. 2353 - 2356
Indexed
SCI; SCIE; SCOPUS scopus
Abstract
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-(hydroxyrnethyl)-β-erythro-pentofuranosyl]adenine (3), was obtained after regioselective ring opening of 15a with adenine and radical-induced deoxygenanon of the extra hydroxyl group. Elsevier Science Ltd.
DOI
10.1016/0040-4039(96)00289-4
Appears in Collections:
약학대학 > 약학과 > Journal papers
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