Practical synthesis of a pyrrolidine analog of a mono-THF acetogenin as a proto-type analog to evaluate the effect of a heteroatom in the mono-THF ring of acetogenins was achieved using Pd(II)-catalyzed diastereo-selective cyclization. Ligand-less PdCl 2 catalyzed cyclization yielded the desired pyrrolidine derivative as a single major product having the desired relative configurations. Coupling of the pyrrolidine fragment with a known γ-lactone-containing fragment via a Sonogashira cross-coupling reaction yielded the desired aza-cis-solamin analog.
|Number of pages||10|
|Publication status||Published - 2015|
ASJC Scopus subject areas
- Analytical Chemistry
- Organic Chemistry