Synthesis of spirocyclic γ-lactones by cascade Beckwith-Dowd ring expansion/cyclization.
A range of spirocyclic γ-lactones have been prepared exploiting a Beckwith-Dowd ring expansion cascade involving 1-, 3-, 4-, and 5-carbon expansion of cyclopentanone and cyclohexanone followed by 5-exo-trig or 5-exo-dig cyclization. This radical cascade reaction can be achieved with various substrates to provide a broad range of γ-lactones spirofused to 6- to 10-membered cycloalkanones.
School of Chemistry, Monash University, Clayton 3800, Victoria, Australia.
Judith
J
Hierold
David W
DW
Lupton
D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D007783:Lactones; D013141:Spiro Compounds