137821-21-7Relevant articles and documents
Nucleophilic openings of bicyclic β-lactones via acyl C-O and alkyl C-O cleavage: Catalytic, asymmetric synthesis of a versatile, carbocyclic nucleoside precursor and protected transpentacin
Yokota, Yasuno,Cortez, Guillermo S,Romo, Daniel
, p. 7075 - 7080 (2002)
A variety of carbocycle-fused β-lactones are accessible via the intramolecular catalytic, asymmetric nucleophile catalyzed aldol-lactonization reaction recently developed in our laboratory. These bicyclic β-lactones undergo facile ring cleavage under mild
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.
Synthesis of pseudo-Ribofuranoses by Stereocontrolled Reactions on 4-Hydroxycyclopent-2-enylmethanol Derivatives
Shoberu, Karoline A.,Roberts, Stanley M.
, p. 2419 - 2426 (2007/10/02)
The diol 3 is a major product formed from a Prins reaction on cyclopentadiene and was readily converted into the derivatives 4-7.The latter compounds were obtained in states of high optical purity by using both enzyme-catalysed hydrolysis and esterificati
