Nepetalactone synthesis

Smoking the leaves of catnip (Nepeta cataria) produces only mild effects in man. However, the pure active agent, cis, trans-nepetalactone, seems not to have been tested on man. Seeds are available from several companies and the freshly picked leaves are probably more potent. Catnip is not orally active in cats, For synthesis see Corsi Semin, chim. 11,93(1968) et seq. BCSJ 22,1737(1960) Proc. Chem. Soc. 166(1963). JOC 37,3376 (1972) gives a synthesis of dihydronepetalactone (more attractive to cats than nepetalactone). 

The total synthesis of cW-nepetalactone itself was achieved a short time earlier by Sakan s group (Scheme 36).300 In their approach, the first bicyclooctenone inter-... 

Different approaches have been proposed for the stereoselective synthesis of methylcyclopentanoid monoterpenes with nepetalactone-type skeleton (3-oxobicyclo[4.3.0]nonan-2-one-type) and iridomirmecin-type skeleton (3-oxobicyclo[4.3.0]nonan-4-one-type). We will divide the discussion on the basis of the key reactions used in the S5mthetic strategy. 

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