title: An expedient protecting-group-free total synthesis of (±)-dievodiamine.
abstract: The first total synthesis of the Evodia rutaecarpa derived natural product dievodiamine is described. The convergent synthesis was performed without protecting groups, delivering a route that is short and high yielding and uses limited chromatography. Key steps include organometallic addition into a DHED adduct and the Stille coupling of two advanced intermediates to complete the synthesis.
authors.affiliation: Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK. william.unsworth@york.ac.uk
authors.forename: William P
authors.initials: WP
authors.lastname: Unsworth
authors.forename: Christiana
authors.initials: C
authors.lastname: Kitsiou
authors.forename: Richard J K
authors.initials: RJ
authors.lastname: Taylor
mesh_terms: D001685:Biological Factors / Q000138:chemical synthesis* / Q000737:chemistry*; D032086:Evodia / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*
chemical_list: D001685:Biological Factors; D006576:Heterocyclic Compounds, 4 or More Rings; D007211:Indoles; D009942:Organometallic Compounds; C585256:dehydroevodiamine hydrochloride; C585255:dievodiamine