Issue 38, 2020

A modular and divergent approach to spirocyclic pyrrolidines


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.

Graphical abstract: A modular and divergent approach to spirocyclic pyrrolidines

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Article information

Article type
Edge Article
03 Jul 2020
06 Aug 2020
First published
07 Aug 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2020,11, 10354-10360

A modular and divergent approach to spirocyclic pyrrolidines

B. D. A. Shennan, P. W. Smith, Y. Ogura and D. J. Dixon, Chem. Sci., 2020, 11, 10354 DOI: 10.1039/D0SC03676E

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