A chemical study of burley tobacco flavour (nicotiana tabacumL.) VI. Identification and Synthesis of Four Irregular Terpenoids Related to Solanone, Including a ‘Prenylsolanone’

Four novel constituents of Burley tobacco condensate have been identified as ( E )‐5‐isopropyl‐7‐(2‐methyl‐tetrahydrofur‐2‐yl)‐hept‐6‐en‐2‐one ( G ), ( E )‐5‐isopropyl‐7‐(2‐methyl‐tetrahydrofur‐2‐yl)‐hept‐6‐en‐2‐ol ( H ), ( E )‐4‐methyl‐7‐isopropyl‐10‐oxo‐undec‐5‐en‐4‐olide ( I ), and ( E , E )‐6,12‐dimethyl‐9‐isopropyltrideca‐5,10,12‐trien‐2‐one ( J ) or ‘prenylsolanone’. Compounds G , H , and I were synthesized from norsolanadione ( 1 ), compound J from solanone ( A ). These substances belong to a growing family of tobacco metabolites structurally related to solanone ( A ). Their possible formation from cembrene‐type precursors is briefly outlined.