1354568-06-1Relevant articles and documents
The Enantioselective Synthesis of Eburnamonine, Eucophylline, and 16′-epi-Leucophyllidine
Hayashida, Kohei,Korch, Katerina M.,Ngamnithiporn, Aurapat,Reimann, Christopher E.,Saito, Daisuke,Stoltz, Brian M.
, p. 17957 - 17962 (2021)
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 Friedl?nder 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.
QUATERNARY HETEROATOM CONTAINING COMPOUNDS
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Page/Page column 93, (2013/02/28)
A compound useful as a building block for the manufacture of various compounds is represented by Formula A or D. In Formula A and D, z is 0 or 1; Q is a heteroatom; Rl through R1 1 and Ra through Rf are each independently hydrogen, a substituted or unsubstituted hydrocarbyl group, a substituted or unsubstituted heteroatom containing hydrocarbyl group, or a functional group; d, e and f are each independently 0 or greater; each of A, B and D is independently a carbon atom or a heteroatom; and two or more of R1 though R1 1, Ra through Rf and Y optionally combine to form a ring. In some embodiments, R8 and R9 combine to form a carbonyl group. In some embodiments, R2 and Y combine to form a ring with the Q atom. In some embodiments, the ring includes at least one double bond.
