223259-04-9Relevant academic research and scientific papers
Formal synthesis of (±)-mitsugashiwalactone and (±)-isodihydronepetalactone from norborn-5-en-2-one involving shapiro reaction
Chang, Meng-Yang,Chang, Nein-Chen
, p. 41 - 45 (1999)
A formal synthesis of (±)-mitsugashiwalactone (1) and (±)-isodihydro nepetalactone (2) was accomplished. Baeyer-Villiger lactonization of ketone 9 followed by acidic treatment led to the rearranged lactone 8, which underwent a series of functional group transformations to give cyclopentanone derivatives 19 and 20. Shapiro reaction on 21 and 22 in the presence of excess dry ice gave lactones 5 and 6. Lactones 5 and 6 previously have been converted to mitsugashiwalactone (1) and isodihydronepetalactone (2), respectively.
