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- Title
The Enantioselective Synthesis of Eburnamonine, Eucophylline, and 16′‐epi‐Leucophyllidine.
- Authors
Reimann, Christopher E.; Ngamnithiporn, Aurapat; Hayashida, Kohei; Saito, Daisuke; Korch, Katerina M.; Stoltz, Brian M.
- Abstract
A synthetic approach to the heterodimeric bisindole alkaloid leucophyllidine is disclosed herein. An enantioenriched lactam building block, synthesized through palladium‐catalyzed asymmetric allylic alkylation, served as the precursor to both hemispheres. The eburnamonine‐derived fragment was synthesized through a Bischler–Napieralski/hydrogenation approach, while the eucophylline‐derived fragment was synthesized by Friedländer quinoline synthesis and two sequential C−H functionalization steps. A convergent Stille coupling and phenol‐directed hydrogenation united the two monomeric fragments to afford 16′‐epi‐leucophyllidine in 21 steps from commercial material.
- Subjects
ALLYLIC alkylation; ALKALOIDS; HYDROGENATION
- Publication
Angewandte Chemie, 2021, Vol 133, Issue 33, p18101
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202106184