Chemoenzymatic access to versatile epoxyquinol synthons.
The enantiomerically pure and readily available metabolites 10-12 have been converted over four simple steps into the epoxyquinol derivatives 22-24, respectively. Compounds 23 and 24 or their immediate precursors have been exploited in efficient total syntheses of (-)-bromoxone (ent-1), (-)-epiepoformin (ent-2), (-)-harveynone (4), (+)-panepophenanthrin (6), and (+)-hexacyclinol (9).
Pinkerton
David M
DM
Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia.
Banwell
Martin G
MG
Willis
Anthony C
AC
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis / Q000737:chemistry; D053138:Cyclohexenes / Q000138:chemical synthesis / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006873:Hydroquinones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D010616:Phenanthrenes / Q000138:chemical synthesis / Q000737:chemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D053138:Cyclohexenes; D004852:Epoxy Compounds; D006873:Hydroquinones; D010616:Phenanthrenes; D011083:Polycyclic Compounds; C415026:bromoxone; C506854:epiepoformin; C538696:harveynone; C469535:hexacyclinol; C468593:panepophenanthrin