title: A concise route to structurally diverse DMP 323 analogues via highly functionalized 1,4-diamines.
abstract: [reaction: see text] The utility of functionalized 1,4-diamines, produced via a temporary phosphorus tether (P-tether)/ring-closing metathesis (RCM)/hydrolysis sequence, is demonstrated in the synthesis of structurally diverse DMP 323 analogues. These 1,4-diamines are transformed into various seven-membered heterocycles via insertion of the appropriate nuclei "X". Subsequent derivatization generates heterocyclic diols that are similar in structure to DMP 323, a notable member of a class of highly potent inhibitors of HIV protease.
authors.affiliation: Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, USA.
authors.forename: Matthew D
authors.initials: MD
authors.lastname: McReynolds
authors.forename: Kevin T
authors.initials: KT
authors.lastname: Sprott
authors.forename: Paul R
authors.initials: PR
authors.lastname: Hanson
mesh_terms: D000438:Alcohols; D001381:Azepines; D003959:Diamines / Q000737:chemistry; D017320:HIV Protease Inhibitors / Q000138:chemical synthesis*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis; D014508:Urea / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
chemical_list: D000438:Alcohols; D001381:Azepines; D003959:Diamines; D017320:HIV Protease Inhibitors; D006571:Heterocyclic Compounds; D014508:Urea; C085816:DMP 323