2. Academic Validation
  3. Ring expansion of azetidinium ylides: rapid access to the pyrrolizidine alkaloids turneforcidine and platynecine

Ring expansion of azetidinium ylides: rapid access to the pyrrolizidine alkaloids turneforcidine and platynecine

  • Org Lett. 2005 Jul 7;7(14):2949-52. doi: 10.1021/ol050915o.
John A Vanecko 1,  F G West
Affiliations

Affiliation

  • 1 Department of Chemistry, University of Utah, Salt Lake City, 84112-0850, USA.
PMID: 15987177 DOI: 10.1021/ol050915o
Abstract

[reaction: see text] Azetidinecarboxylate esters react readily with metallocarbenes in an inter- or intramolecular fashion to generate azetidinium ylides. Efficient [1,2]-shift by the ester-substituted carbon furnishes ring-expanded pyrrolidine products. In the case of substrate 1, this provides access to the Pyrrolizidine Alkaloids turneforcidine and platynecine via a high-yield, five-step sequence starting with readily available methyl 1-benzylazetidine-2-carboxylate.

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