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Query: faculty: "FNWI" and publication year: "2010"

AuthorFinbar Schutte
TitleApproach to the synthesis of indolealkaloids by phosphonate-based chemistry
SupervisorMartin J. Wanner
Year2010
Pages30
FacultyFaculty of Science
ProgrammeFNWI BSc Scheikunde
AbstractA synthetic route towards apo-yohimbine and geissoschizine, based on phosphonate chemistry and enantioselective catalytic Pictet-Spengler reactions has been explored. The phosphonate functional group containing aldehyde needed for this route has been synthesized, and proved able to undergo Pictet-Spengler reactions with different N-allyl-tryptamine derivatives. The ee’s of these reactions covered a very wide range, from a (nearly) racemic mixture up to 84% ee, depending on both the catalyst and tryptamine-derivative. The targeted final products apo-yohimbine and geissoschizine could not be obtained, due to problems with the cyclizations steps (e.g. a Heck-reaction) required for their synthesis. Also, a novel route towards some spiro-compounds was explored. For this route, the synthesis of a bis-sulphone containing C4-aldehyde was prepared. A bisphosphonate analogue could not be synthesized. The bis-sulphonic aldehyde was then used in a Pictet-Spengler reaction, which yielded the normal β-carboline Pictet-Spengler product, instead of the spiro-product.
Document type scriptie bachelor
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