151477-94-0Relevant articles and documents
Concise Racemic and Highly Enantioselective Approaches to Key Intermediates for the Syntheses of Carbocyclic Nucleosides and pseudo-Ribofuranoses: Formal Syntheses of Carbovir
Hodgson, David M.,Witherington, Jason,Moloney, Brian A.
, p. 3373 - 3378 (2007/10/02)
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-oxabicyclohexane-3-methanol 13 (also prepared from the acid 4) using the dilithium salt of (1S,2R)-norephedrine.