Asymmetric synthesis of 6'-hydroxyarenarol: the proposed biosynthetic precursor to popolohuanone E.
The first synthesis of (+)-6'-hydroxyarenarol 3, the proposed biogenetic precursor to popolohuanone E (1), is described. An enantioselective route to key iodide intermediate 12 has been developed allowing the asymmetric synthesis of the known cis-decalin 22. Conditions which allow the removal of the methyl ether protecting groups on the hydroxyarene leaving the exocyclic methylene moiety in tact have also been developed to complete this synthesis.
Munday
Rachel H
RH
School of Chemistry, University of Nottingham, Nottingham, NG7 2RD, United Kingdom.
Denton
Ross M
RM
Anderson
James C
JC
D001572:Benzofurans / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D010636:Phenols / Q000138:chemical synthesis*; D011083:Polycyclic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
C534370:6'-hydroxyarenarol; D001572:Benzofurans; D009281:Naphthalenes; D010636:Phenols; D011083:Polycyclic Compounds; C510740:popolohuanone E; C007229:decalin