Structure-based organic synthesis of a tricyclic N-malayamycin analogue.
The solid-state structure of crystalline malayamycin A reveals a urea substituent that bisects the plane of the chairlike tetrahydropyran subunit. On the basis of this topological feature, we synthesized a tricyclic N-nucleoside analogue in which an ethano bridge linked the urea NH group with the ring junction of the bicyclic tetrahydrofuropyran unit.
Hanessian
Stephen
S
Department of Chemistry, Université de Montréal, C. P. 6128, Succursale Centre-Ville, Montréal, Québec H3C 3J7, Canada. stephen.hanessian@umontreal.ca
Ritson
Dougal J
DJ
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014508:Urea / Q000737:chemistry
D019086:Bridged Bicyclo Compounds, Heterocyclic; D009705:Nucleosides; C493874:malayamycin A; D014508:Urea