308287-84-5Relevant academic research and scientific papers
Synthesis of (1R, 3R)-3-[2-(aminoethyl)-2,2-dimethylcyclobutyl]methanol and (1S,3R)-(3-amino-2,2-dimethylcyclobutyl)methanol from (+)-nopinone
Figueira,Blanco,Caamano,Fernandez,Garcia-Mera,Lopez
, p. 1459 - 1463 (2000)
The title amino alcohols 6 and 7, which are of interest as intermediates in the synthesis of carbocyclic analogs of nucleosides, were synthesized from (+)-nopinone (8). Ring opening of α-isonitrosonopinone leads to a cyanoester which can be directly reduced to 6. Alternatively, a longer route from the lactam 12, one of the Beckmann rearrangement products of 8, leads also to 6, in a higher overall yield. Besides this the isomeric lactam 13 was transformed, upon hydrolytic opening, oxidative degradation of the lateral chain and reduction, into 7.
Stereodivergent synthesis of the first bis(cyclobutane) γ-dipeptides and mixed γ-oligomers
Aguilera, Jordi,Moglioni, Albertina G.,Moltrasio, Graciela Y.,Ortuno, Rosa M.
, p. 302 - 308 (2008/09/19)
Diastereomeric bis(cyclobutane) γ-dipeptides, a new class of γ-peptides, have been synthesized efficiently from both enantiomers of conveniently protected 3-amino-2,2-dimethyl-1-carboxylic acid. These amino acids have been prepared in very good overall yields through enantiodivergent synthetic routes starting from (-)-cis-pinononic acid. Mixed γ-oligomers have also been prepared from GABA and cyclobutane residues.
Stereoselective synthesis of chiral precursors to cyclobutane carbocyclic nucleosides and oligopeptides
Rouge, Pablo D.,Moglioni, Albertina G.,Moltrasio, Graciela Y.,Ortuno, Rosa M.
, p. 193 - 196 (2007/10/03)
Versatile and highly efficient synthetic routes leading to optically active cyclobutanones, γ-amino acids and δ-amino alcohols are described. These compounds are relevant synthetic precursors to enantiopure cyclobutane carbocyclic nucleosides and oligopeptides. (-)-(S)-Verbenone is the chiral starting material used and the key synthetic steps involve concerted rearrangements in acidic medium.
