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II. C-nucleosides and related compounds carbocyclic analogues of C-nucleosides: A useful intermediate

✍ Scribed by George Just; Grant Reader

Publisher: Elsevier Science
Year: 1973
Tongue: French
Weight: 150 KB
Volume: 14
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)95987-8

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✦ Synopsis

Pyrazomycln (I)l and showdomycln*, a closely related compound, have been recently syntheslzed starting from the rlbose derlvatlve II'. We w1s.h to report the synthesis of a carboxycllc analogue of II (IX), which should be a useful intermediate to prepare carbocycllc analogues of pyrazomycln. A somewhat similar approach has been used by Shealy and coworkers for the preparation of carboxycllc analogues of purlne rlbo and deoxyrlbonucleosldes. 3,4,5 6,7 Diels-Alder adduct III , which can be obtained In good yield from cyclopentadlene and bromoacryllc acid, was esterlfled with diazomethane, and the methyl ester hydroxylated by catalytic osmylation. 8 Dial VI, m-p. 144-5',

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