Spiro-fused Pyrrolidine, Piperidine, and Oxindole Scaffolds from Lactams

Christoph Hirschhauser, Jeremy S. Parker, Matthew W. D. Perry, Mairi I. F. Haddow, Tim C Gallagher

Research output: Contribution to journalArticle (Academic Journal)peer-review

27 Citations (Scopus)

Abstract

Expedient routes to three classes of novel spiro-fused pyrrolidine, piperidine, and indoline heterocycle scaffolds are described. These three-dimensional frameworks, which conform to the "rule of three", are suitably protected to allow for site-selective manipulation and functionalization. Different modes of substrate control were explored, which allow for good to excellent levels of diastereoselectivity and dispense with the need for additional chiral reagents or catalysts. The concepts developed were applied in short, formal syntheses of (+/-)-coerulescine and (+/-)-horsfiline.

Original languageEnglish
Pages (from-to)4846-4849
Number of pages4
JournalOrganic Letters
Volume14
Issue number18
DOIs
Publication statusPublished - 21 Sep 2012

Keywords

  • STEREOSELECTIVE-SYNTHESIS
  • SNAR REACTIONS
  • ALKALOIDS
  • ACID

Fingerprint Dive into the research topics of 'Spiro-fused Pyrrolidine, Piperidine, and Oxindole Scaffolds from Lactams'. Together they form a unique fingerprint.

Cite this