Concise racemic and highly enantioselective approaches to key intermediates for the syntheses of carbocyclic nucleosides and pseudo-ribofuranoses: formal syntheses of carbovir

1 January 1994

journal article
Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1

No. 23,p. 3373-3378
https://doi.org/10.1039/p19940003373

Abstract

A regio- and stereo-specific synthesis of cis-(±)-3-acetoxy-5-(acetoxymethyl)cyclopentene 3 from cyclopent-3-enecarboxylic acid 4via 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 the acid 4) using the dilithium salt of (1S,2R)-norephedrine.

Keywords

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