From cyclopentadiene to isoxazoline-carbocyclic nucleosides: a rapid access to biological molecules through aza-Diels-Alder reactions

A rapid access to carbocyclic nucleosides containing a fused isoxazoline ring is proposed through the Grieco cycloaddition of cyclopentadiene to iminium salts. The prolific elaboration of the isoxazoline cycloadducts allowed preparation of the target aminols through the unmasking of the hydroxymethylene group at the C3 level of the azanorbornene structure. The heterocyclic aminols are readily converted into nucleosides via the linear construction of purine heterocycles.

Graphical abstractA rapid access to carbocyclic nucleosides containing a fused isoxazoline ring is proposed through the Grieco cycloaddition of cyclopentadiene to iminium salts. The prolific elaboration of the isoxazoline cycloadducts allowed preparation of the target aminols through the unmasking of the hydroxymethylene group at the C3 level of the azanorbornene structure. The heterocyclic aminols are readily converted into nucleosides via the linear construction of purine heterocycles. Download full-size image