Details

Autor(en) / Beteiligte

• Toop, Hamish D.
• Brusnahan, Jason S.
• Morris, Jonathan C.

Titel

Concise Total Synthesis of Dioncophylline E through an ortho‐Arylation Strategy

Ist Teil von

• Angewandte Chemie International Edition, 2017-07, Vol.56 (29), p.8536-8538

Ort / Verlag

Germany

Erscheinungsjahr

2017

Link zum Volltext

Quelle

MEDLINE

Beschreibungen/Notizen

• The first total synthesis of the potent antimalarial 7,3′‐linked naphthylisoquinoline alkaloid dioncophylline E (1) has been completed. The synthesis proceeds in 12 steps (longest linear sequence) and in 15 % overall yield. Key transformations include an ortho‐arylation of a naphthol with an aryllead triacetate to construct the sterically hindered biaryl bond, and a three‐step sequence to stereoselectively generate the trans‐1,3‐dimethyl‐1,2,3,4‐tetrahydroisoquinoline moiety. Access granted: Total synthesis of the potent antimalarial 7,3′‐linked naphthylisoquinoline alkaloid dioncophylline E was achieved. The synthesis proceeds in 12 steps (longest linear sequence) and 15 % overall yield. Key transformations include an ortho‐arylation of a naphthol with an aryllead triacetate to give the sterically hindered biaryl bond, and a three‐step sequence to stereoselectively generate the trans‐1,3‐dimethyl‐1,2,3,4‐tetrahydroisoquinoline moiety.