197232-94-3

Upstream product

• 197232-93-2 2-[(1R,2R,6R)-3-acetyloxy-1,2-dimethyl-6-(1-methylvinyl)cyclohex-3-enyl]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 
• 197232-88-5 (1S,3R,4R,5S)-4-(2-hydroxyethyl)-3,4,6,6-tetramethylbicyclo[3.1.1]heptan-2-ol 
• 134655-24-6 (1S,4R,5R)-4,6,6-trimethyl-4-vinylbicyclo[3.1.1]heptan-2-one 
• 197232-92-1 2-[(1S,2R,3R,5S)-2,3,6,6-tetramethyl-4-oxobicyclo[3.1.1]hept-2-yl]ethyl acetate 

Downstream Products

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

Relevant academic research and scientific papers

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.

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.