22981-83-5Relevant academic research and scientific papers
Synthesis and evaluation of new chiral diols based on the dicyclopentadiene skeleton
Borsato, Giuseppe,De Lucchi, Ottorino,Fabris, Fabrizio,Lucchini, Vittorio,Frascella, Pietrogiulio,Zambon, Alfonso
, p. 3517 - 3520 (2003)
The resolution by Lipase PS of rac-5 (from reduction of ketone 6, obtained from dicyclopentadiene with a new environment-friendly synthesis) gives (2S)-5, which was further reduced to the endo (2R)-1a alcohol. The endo (2S)-1b alcohol was obtained from camphor with a multistep synthesis. Pinacol couplings of 3a,b, carried out with Mg/Hg or Corey's general procedure respectively, afforded with high diastereoselectivity the C2 symmetry diols (2R,2′R)-2a and (2S,2′S)-2b, with endo oriented OH functions. The enantiogenic power of the endo alcohol (2R)-1a and (2S)-1b and of the diols (2R,2′R)-2a and (2S,2′S)-2b was tested towards the LiAlH4 reduction of acetophenone. The C2 symmetry appears to play a fundamental role.
Copper(I)-catalyzed intramolecular photocycloadditions of dicyclopentadiene derivatives linked by removable tethers
Chebolu, Ravikrishna,Zhang, Wei,Galoppini, Elena,Gilardi, Richard
, p. 2831 - 2834 (2000)
Cu(I)-catalyzed intramolecular [2+2] photocycloadditions of two dicyclopentadiene derivatives linked by an alkyl chain have been studied. These reactions are regio- and stereoselective and proceed considerably faster than the corresponding intermolecular reactions. (C) 2000 Elsevier Science Ltd.
SYNTHESIS OF dl-CORIOLIN
Ito, Toshio,Tomiyoshi, Nobuya,Nakamura, Koki,Azuma, Shizuo,Izawa, Makoto,et al.
, p. 241 - 255 (2007/10/02)
The total synthesis of dl-coriolin has been achieved in a stereoselective way.The key tricyclic intermediate was synthesized from dicyclopentadiene through a route which involved an SN2 reaction at a neopentylic position.
A NEW SYNTHESIS OF dl-CORIOLIN A. APPLICATION OF A NEW SN2 REACTION AT A NEOPENTYLIC POSITION
Ito, Toshio,Tomiyoshi, Nobuya,Nakamura, Koki,Azuma, Shizuo,Izawa, Makoto,et. al
, p. 1721 - 1724 (2007/10/02)
Dicyclopentadiene has been stereoselectively converted to a key tricyclic intermediate for the total synthesis of coriolin, through a route which involves a new SN2 reaction at a neopentylic position.
