A new synthesis of dl-muscopyridine based on the regioselective cyclopentenone annulation

Article abstract of DOI:10.1016/0040-4039(80)80210-3

Sulphuric acid catalyzed ring closure of propargyl alcohol dianion adduct of 2-cyclododecenone gives bicyclo[10.3.0]pentadec-1(12),2-dien-13-one. 1,6-Conjugate addition of methyl group followed by ring-expansion and aromatization affords the title compounds.