One-pot synthesis of polycyclic nucleosides with unusual molecular skeletons.
An alpha hydroxy pyrrolidine tricyclic nucleoside 3 and its spontaneous reaction with acetone is described. In this transformation highly functionalized polycyclic nucleosides with rather unusual molecular skeletons are formed in a complete regio- and stereoselective way. The reaction involves the formation of three new bonds, two of them novel carbon-carbon bonds, in a one-pot way. An enamine-iminium mechanism with participation of carbinolamine, iminium ion, and enamine intermediates is proposed as a plausible explanation for this transformation. The scope of the reaction is briefly studied concluding that the nature of the ketone (R(1)COR(2)) is critical for the initial attack of the NH to the carbonyl group.
Bonache
María-Cruz
MC
Instituto de Química Médica (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain.
Cordeiro
Alessandra
A
Carrero
Paula
P
Quesada
Ernesto
E
Camarasa
María-José
MJ
Jimeno
María-Luisa
ML
San-Félix
Ana
A
D000096:Acetone / Q000737:chemistry; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis*; D055601:Organic Chemistry Phenomena; D011083:Polycyclic Compounds / Q000138:chemical synthesis*; D011759:Pyrrolidines
D009705:Nucleosides; D011083:Polycyclic Compounds; D011759:Pyrrolidines; D000096:Acetone