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CONCISE RACEMIC AND HIGHLY ENANTIOSELECTIVE APPROACHES TO KEY INTERMEDIATES FOR THE SYNTHESES OF CARBOCYCLIC NUCLEOSIDES AND PSEUDO-RIBOFURANOSES - FORMAL SYNTHESES OF CARBOVIR

Abstract:

A regio- and stereo-specific synthesis of cis-(±)-3-acetoxy-5- (acetoxymethyl)cyclopentene 3 from cyclopent-3-enecarboxylic acid 4 via a bromolactonisation strategy is described. Pd-catalysed coupling of the cis-(±)-diacetate 3 with 2-amino-6-chloropurine or 2,6-diaminopurine leads to the formal syntheses of carbovir 1. A synthesis of the (1R)-cis-diacetate 15 (R = Ac) is described via a highly enantioselective rearrangement of cis-6-oxabicyclo[3.1.0]hexane-3-methanol 13 (also prepared from t...

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Publication status:
Published

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Publisher copy:
10.1039/p19940003373

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Journal:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Issue:
23
Pages:
3373-3378
Publication date:
1994-12-07
DOI:
EISSN:
1364-5463
ISSN:
0300-922X
URN:
uuid:1e14f932-6ed5-4d98-8d1d-2fa08f733cf2
Source identifiers:
52145
Local pid:
pubs:52145
Language:
English

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