65470-96-4

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 120-92-3 cyclopentanone 
• 5530-96-1 endo-tricyclo[5.2.1.0(2,6)]deca-4,8-dien-3-one 
• 1755-01-7 endo-Dicyclopentadien 
• 875-20-7 5-exo-hydroxytricyclo[5.2.1.0(2,6)]deca-3,8-diene 
• 22981-84-6 (3aS^*,4R^*,7S^*,7aR^*)-2,3,4a,4,7,7a-hexahydro-4,7-methano-1H-inden-1-one 

Downstream Products

• 31351-12-9 (3aR^*,4S^*,7S^*,7aR^*)-2,3,3a,4,5,6,7,7a-octahydro-4,7-methano-1H-inden-5-one 
• 10271-45-1 (3aR^*,4S^*,5R^*,7S^*,7aR^*)-2,3,3a,4,5,6,7,7a-octahydro-5-hydroxy-4,7-methano-1H-indene 
• 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

Linearly Fused vs Bridged Regioselection in the Intramolecular 1,3-Diyl Trapping Reaction

The intramolecular diyl trapping reaction can now be used to obtain synthetically useful quantities of either bridged or linearly fused cycloadducts in a selective manner and by design.Bridged cycloadducts arise by intercepting the triplet diyl, while linearly fused products can be produced from either the singlet or the triplet.When an electron-withdrawing group is attached to the diylophile , the singlet diyl leads selectively to fused cycloadducts.On the other hand , the presence of a large alkyl group attached to the internal carbon of the diylophile affords bridged cycloadducts selectively from cycloaddition with the triplet.Four diazenes, 4-7, differing only in the electronic and steric properties of the substituent located on the internal carbon of the diylophile, were studied.The diyl trapping reactions were conducted using ca. 1 mM solutions of diazene in THF at reflux for periods of 3-4h; cycloadduct yields ranged from 68percent ( beginning with the dimethyl ketal 7) to 98percent ( from keto diazene 4).To determine the origin of the bridged cycloadducts, the effect of oxygen upon the product distribution was examined.The results show that the rate of the intramolecular triplet diyl cycloaddition is slower than the rate of the intermolecular reaction of the triplet with oxygen.The rate of triplet intramolecular cycloaddition can be estimated to be less than 4 x 106 to 4 x 107 s-1.

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.

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.

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.