Issue 38, 2020

A modular and divergent approach to spirocyclic pyrrolidines

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.

Graphical abstract: A modular and divergent approach to spirocyclic pyrrolidines

Supplementary files

Article information

Article type
Edge Article
Submitted
03 7 2020
Accepted
06 8 2020
First published
07 8 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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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