90546-07-9

Upstream product

• 5530-96-1 endo-tricyclo[5.2.1.0(2,6)]deca-4,8-dien-3-one 
• 875-20-7 5-exo-hydroxytricyclo[5.2.1.0(2,6)]deca-3,8-diene 
• 1755-01-7 endo-Dicyclopentadien 

Downstream Products

• 22981-84-6 (3aS^*,4R^*,7S^*,7aR^*)-2,3,4a,4,7,7a-hexahydro-4,7-methano-1H-inden-1-one 
• 137824-15-8 3-phenyltricyclo<5.2.1.0^2,6>dec-8-en-endo-3-ol 

Relevant academic research and scientific papers

SYNTHESIS OF dl-CORIOLIN

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.

Synthesis and evaluation of new chiral diols based on the dicyclopentadiene skeleton

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

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.

A NEW SYNTHESIS OF dl-CORIOLIN A. APPLICATION OF A NEW SN2 REACTION AT A NEOPENTYLIC POSITION

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.