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Thursday, August 27 • 3:40pm - 4:00pm
[0065] Biomimetic Synthesis of Phenylethanoid Alkaloids

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The phenylethanoids are a diverse group of shikimic acid derived natural products, characterised by the presence of a C6C­2 moiety.  These compounds are of great interest for their structural complexity and wide range of biological functions. Incargranine B is a dimeric phenylethanoid alkaloid, originally assigned an unprecedented indolo[1.7]naphthyridine structure. As a result of biosynthetic speculation, we proposed a dipyrroloquinoline core as a plausible alternative structure.  Following a biomimetic strategy, the proposed structure of incargranine B was accessed in six steps, confirming the suggested structural revision and indicating the natural product likely exists as a mixture of two pseudo-enantiomeric diastereomers. Extending upon this biomimetic synthesis, we now propose a unified biosynthetic hypothesis for the entire family of phenylethanoid natural products isolated from plants of the genus incarvillea. Studies towards the biomimetic synthesis of millingtonine and incargranine A will also be presented.

ST Lecturers
avatar for Patrick Brown

Patrick Brown

PhD Candidate, University of Edinburgh
Graduate StudentUniversity of Edinburgh

Thursday August 27, 2015 3:40pm - 4:00pm PDT
Girvetz 2119