197232-93-2

Upstream product

• 108-24-7 acetic anhydride 
• 197232-92-1 2-[(1S,2R,3R,5S)-2,3,6,6-tetramethyl-4-oxobicyclo[3.1.1]hept-2-yl]ethyl acetate 
• 80-57-9 (-)-Verbenone 
• 197232-90-9 2-[(1S,2R,3R,5S)-4-hydroxy-2,3,6,6-tetramethylbicyclo[3.1.1]hept-2-yl]ethyl acetate 
• 197232-86-3 (1S,3R,4R,5S)-3,4,6,6-tetramethyl-4-vinylbicyclo[3.1.1]heptan-2-one 
• 134655-24-6 (1S,4R,5R)-4,6,6-trimethyl-4-vinylbicyclo[3.1.1]heptan-2-one 

Downstream Products

• 197232-94-3 (2S,3R,4R)-3-(2-hydroxyethyl)-2,3-dimethyl-4-(1-methylvinyl)cyclohexan-1-one 
• 197232-95-4 2-[(1R,2S,6R)-1,2-dimethyl-6-(1-methylvinyl)-3-oxocyclohexyl]ethyl acetate 

Relevant academic research and scientific papers

Stereocontrolled synthesis of the key intermediate for the enantioselective synthesis of clerodane natural products

Stereocontrolled synthesis of (+)-trans-decalone 7 (R = CH=CH2) from (-)-verbenone (5), readily obtainable from (+)-nopinone (2), is described. The compound 7 possesses four correctly arranged chiral centers, C(5)-C(10)-C(9)-C(8), necessary for the enantioselective synthesis of neo-trans-clerodanes.

New entry to the synthesis of clerodane diterpenes. The first enantioselective syntheses of 7-oxo-kolavenic acid and methyl solidagonate

Using (1S,5S)-(-)-verbenone (8b), readily obtainable from (+)-nopinone (3), as the chiral source, we have established the general method for preparation of three kinds of key intermediates, conjugate enones 9 and 10 for the syntheses of neo-trans-clerodanes and 11 for those of neo-cis-clerodanes. Starting with the compound 10, the first enantioselective syntheses of (-)-(5R,8S,9S,10R)-7-oxo-cleroda-3,13E-dien-15-oic acid (7-oxo-kolavenic acid) (1) and solidagonic acid (2) as its methyl ester (48) were achieved.