689290-74-2Relevant articles and documents
Preparation of optically pure cross-conjugated cyclopentadienones
Eddolls, Jonathan P.,Iqbal, Mazhar,Roberts, Stanley M.,Santoro, M. Gabriella
, p. 2539 - 2550 (2004)
The synthesis of optically pure cross-conjugated cyclopentadienones is readily achieved in two steps via a one-pot alkylcuprate addition/aldol condensation/dehydration sequence using racemic or enantioenriched endo-3a,4,7,7a-tetrahydro-1H-4,7-methano-inden-1-ones followed by microwave-mediated Lewis acid-catalysed retro Diels-Alder reaction. An alternative route involving a modified Baylis-Hillman protocol followed by conjugate addition with alkylcuprates and a retro Diels-Alder reaction was also investigated.
Conjugate addition-Peterson olefination reactions: Expedient routes to cross conjugated dienones
Iqbal, Mazhar,Evans, Paul
, p. 5741 - 5745 (2003)
The synthesis of 5-alkylidenecyclopent-2-enones is readily achieved in two steps via a one-pot conjugate addition-Peterson olefination sequence, using exo-2-trimethylsilyl-3a,4,7,7a-tetrahydro-4,7-methanoinden-1-one, followed by a retro-Diels-Alder reaction.
The conjugate addition-Peterson olefination reaction for the preparation of cross-conjugated cyclopentenone, PPAR-γ ligands
Iqbal, Mazhar,Duffy, Patricia,Evans, Paul,Cloughley, George,Allan, Bernard,Lledo, Agusti,Verdaguer, Xavier,Riera, Antoni
supporting information; experimental part, p. 4649 - 4661 (2009/03/12)
5-Alkylidenecyclopent-2-enones 15a-q may be prepared via a conjugate addition-Peterson olefination sequence, best achieved in one-pot, using exo-2-trimethylsilyl-3a,4,7,7a-tetrahydro-4,7-methanoinden-1-one 12, followed by a retro-Diels-Alder reaction. The geometry of the exocyclic alkene may be controlled according to the use of organometallic species in the conjugate addition step; organocuprate reagents are found to selectively lead to the formation of E-exocyclic alkene adducts, whereas Grignard reagents favour the formation of Z-alkenyl isomers. The use of enantiomerically enriched 12, accessed from an asymmetric Pauson-Khand reaction, affords the corresponding enantioenriched 5-alkylidenecyclopent-2-enones and this approach is exemplified by the short, stereoselective total syntheses of two cyclopentenone phytoprostanes 51 and 13,14-dehydrophytoprostane J165. The ability of this family of synthetic compounds to activate the peroxisome proliferator activated receptor-γ is reported.
