TitleTotal synthesis and conformational study of ovalifoliolatin B
Publication TypeJournal Article
Year of Publication2020
AuthorsM. Salih Q, Zakharov LN, Beaudry CM
JournalTetrahedron Letters
Volume61
Pagination151988
ISSN0040-4039
KeywordsConformational chirality, Reduction, total synthesis, Ullmann coupling
Abstract

The diaryletherheptanoid natural product, ovalifoliolatin B, was synthesized. The synthesis features a regioselective reduction of a conjugated dienone and an intramolecular Ullmann etherification. The conformation of the natural product was studied by dynamic NMR methods and by X-ray crystallography. Although the natural product structure is strained, it has a relatively low barrier for interconversion of enantiomeric conformations.

URLhttp://www.sciencedirect.com/science/article/pii/S0040403920304317
DOI10.1016/j.tetlet.2020.151988