245485-72-7Relevant 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
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.
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 (2007/10/03)
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.
