title: Convergent total syntheses of the Amaryllidaceae alkaloids lycoranine A, lycoranine B, and 2-methoxypratosine.
abstract: The title alkaloids, 1, 2, and 3 respectively, have been prepared in a convergent manner by two related routes. The superior one involves C-H functionalization of the relevant 5-methoxyindole at C-7 using Hartwig's protocol and thus forming the corresponding borolated indole that could be coupled with the requisite 2-bromobenzoate to deliver the title natural products. Single crystal X-ray analyses of the synthetically derived samples of compounds 1 and 2 are reported.
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra ACT 0200, Australia.
authors.forename: Hye Sun
authors.initials: HS
authors.lastname: Kim
authors.forename: Martin G
authors.initials: MG
authors.lastname: Banwell
authors.forename: Anthony C
authors.initials: AC
authors.lastname: Willis
mesh_terms: D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D019668:Liliaceae / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D047151:Amaryllidaceae Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; C541673:lycoranine A; C541674:lycoranine B