245485-69-2Relevant academic research and scientific papers
Enantioselective syntheses of (-)-7-oxo-kolavenic acid and (-)-methyl solidagonate from (-)-verbenone
Kato, Michiharu,Kosugi, Hiroshi,Ichiyanagi, Tsuyoshi,Suzuki, Takao,Kodaira, Ariko,Drechsel, Peter,Hagiwara, Hisahiro
, p. 5377 - 5378 (1999)
The first enantioselective synthesis of the title neo-trans-clerodanes 3 and 4b from (-)-verbenone 5 has been accomplished using the ene reaction and stereoselective conjugate addition reaction to the enone 13 as the key step.
New entry to the synthesis of clerodane diterpenes. The first enantioselective syntheses of 7-oxo-kolavenic acid and methyl solidagonate
Kato, Michiharu,Kosugi, Hiroshi,Ichiyanagi, Tsuyoshi,Hagiwara, Hisahiro,Kodaira, Ariko,Kusakari, Takashi,Suzuki, Takao,Ando, Minako,Lee, Jasmine,Drechsel, Peter,Vogler, Bernhard
, p. 8243 - 8256 (2007/10/03)
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.
