A racemic synthesis of an AB-ring system of hexacyclinic acid.
[structure: see text] An AB-ring system of the polyketide natural product hexacyclinic acid has been synthesized in racemic form. The key steps were an intramolecular Diels-Alder cyclization of an ester tethered 1,3-nonadiene-8-yne, which generated the B-ring, and a samarium diiodide mediated reductive annulation, which was used to form the A-ring.
Clarke
Paul A
PA
School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, United Kingdom. paul.clarke@nottingham.ac.uk
Cridland
Andrew P
AP
D000447:Aldehydes / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D006576:Heterocyclic Compounds, 4 or More Rings; D007783:Lactones