3 research outputs found
One-Pot Synthesis of Polycyclic Nucleosides with Unusual Molecular Skeletons
An R 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 (R1COR2) is critical for the initial
attack of the NH to the carbonyl group.We thank Susana Ruiz for excellent
technical assistance. The Spanish MEC/MCINN (project
SAF 2006-12713-C02-01) and the Comunidad de Madrid
(project BIPEDD-CM S-B10-0214-2006) are also acknowl-
edged for financial support. The Spanish Consejo Superior
de Investigaciones Cientı´ ficas is also acknowledged for a
JAE-Doc contract to M.-C.B.Peer reviewe
One-Pot Synthesis of Polycyclic Nucleosides with Unusual Molecular Skeletons
An R 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 (R1COR2) is critical for the initial
attack of the NH to the carbonyl group.We thank Susana Ruiz for excellent
technical assistance. The Spanish MEC/MCINN (project
SAF 2006-12713-C02-01) and the Comunidad de Madrid
(project BIPEDD-CM S-B10-0214-2006) are also acknowl-
edged for financial support. The Spanish Consejo Superior
de Investigaciones Cientı´ ficas is also acknowledged for a
JAE-Doc contract to M.-C.B.Peer reviewe