A concise route to structurally diverse DMP 323 analogues via highly functionalized 1,4-diamines.
[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.
McReynolds
Matthew D
MD
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, USA.
Sprott
Kevin T
KT
Hanson
Paul R
PR
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*
D000438:Alcohols; D001381:Azepines; D003959:Diamines; D017320:HIV Protease Inhibitors; D006571:Heterocyclic Compounds; D014508:Urea; C085816:DMP 323