Enantiospecific Synthesis of 5′-Noraristeromycin and its 7-Deaza Derivative and A Formal Synthesis of (-)-5′-Homoaristeromycin
- 1 March 1993
- journal article
- Published by Taylor & Francis in Nucleosides and Nucleotides
- Vol. 12 (3-4), 267-278
- https://doi.org/10.1080/07328319308017825
Abstract
Beginning with the treatment of the diacetate of cis-3,5-cyclopentenediol (5) with Pseudomonas cepacia lipase, (-)-5′-noraristeromycin (1) and (-)-7-deaza 5′-noraristeromycin (3) have been prepared. Subjecting 5 to treatment with porcine liver esterase led to an efficient preparation of a substituted cyclopentane precursor which, following literature precedence, can be converted into (-)-5′-homoaristeromycin (4).Keywords
This publication has 19 references indexed in Scilit:
- The synthesis and antiviral properties of (.+-.)-5'-noraristeromycin and related purine carbocyclic nucleosides. A new lead for anti-human cytomegalovirus agent designJournal of Medicinal Chemistry, 1992
- 4'-Modified analogs of aristeromycin and neplanocin A: synthesis and inhibitory activity toward S-adenosyl-L-homocysteine hydrolaseJournal of Medicinal Chemistry, 1992
- Chemoenzymatic synthesis of (-)-carbocyclic 7-deazaoxetanocin GTetrahedron Letters, 1992
- Pseudomonas fluorescens lipase in asymmetric synthesisTetrahedron: Asymmetry, 1991
- The synthesis of two 2′-deoxy carbocyclic purine nucleosides lacking the 5′-methyleneTetrahedron Letters, 1990
- Enantioselective preparation of functionalized cyclopentanoids via a common chiral (.pi.-allyl)palladium complexThe Journal of Organic Chemistry, 1989
- The Synthesis of Derivatives of 2-Arylamino ara-Carbocyclic Purine Nucleosides as Potential Anti-Viral AgentsNucleosides, Nucleotides and Nucleic Acids, 1989
- A highly enantioselective hydrolysis ofTetrahedron Letters, 1986
- A palladium-catalyzed route to mono- and diprotectedTetrahedron Letters, 1985
- 26. Pyrrolo[2,3-d]pyrimidinesJournal of the Chemical Society, 1960