faculty: "FNWI" and publication year: "2010"
| Author||Finbar Schutte|
|Title||Approach to the synthesis of indolealkaloids by phosphonate-based chemistry|
|Supervisor||Martin J. Wanner|
|Faculty||Faculty of Science|
|Programme||FNWI BSc Scheikunde|
|Abstract||A 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|
Use this url to link to this page: http://dare.uva.nl/en/scriptie/364029
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