Abstract
An efficient three-step sequence to afford a valuable class of spirocyclic pyrrolidines is reported. A reductive cleavage/Horner–Wadsworth–Emmons cascade facilitates the spirocyclisation of a range of isoxazolines bearing a distal β-ketophosphonate. The spirocyclisation precursors are elaborated in a facile and modular fashion, via a [3 + 2]-cycloaddition followed by the condensation of a phosphonate ester, introducing multiple points of divergence. The synthetic utility of this protocol has been demonstrated in the synthesis of a broad family of 1-azaspiro[4,4]nonanes and in a concise formal synthesis of the natural product (±)-cephalotaxine.
Highlights
The synthetic utility of this protocol has been demonstrated in the synthesis of a broad family of 1-azaspiro[4,4]nonanes and in a concise formal synthesis of the natural product (Æ)-cephalotaxine
The pyrrolidine ring system is common to numerous pharmaceutical compounds and natural products of structural and biological importance
There is a widespread abundance of the pyrrolidine scaffold within the architecturally complex polycyclic ring systems of natural products
Summary
The pyrrolidine ring system is common to numerous pharmaceutical compounds and natural products of structural and biological importance. An efficient three-step sequence to afford a valuable class of spirocyclic pyrrolidines is reported.
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
