Improving the synthetic route towards linearly fused Tröger’s base analogues
(2019) KEMR31 20191Department of Chemistry
- Abstract
- The route towards linearly fused heptakis-Tröger’s base was followed using a 12 step synthesis route. Hope remains that the final compound will be purified to a satisfactory level within the near future. Additionally, characterizations of reaction intermediates has been completed, up to monoprotected tris-Tröger’s base which has been submitted for its final characterizations. A specifically designed Tröger’s Base analogue was synthesized by functionalizing the benzylic position in the diazocine bridge, with (R)-menthyl ester groups, to make successful separation of previously enantiomeric Tröger’s base analogues possible. Tröger’s Base analogue, containing the bulkier ester side chain, was progressed through, to allow condensation to the... (More)
- The route towards linearly fused heptakis-Tröger’s base was followed using a 12 step synthesis route. Hope remains that the final compound will be purified to a satisfactory level within the near future. Additionally, characterizations of reaction intermediates has been completed, up to monoprotected tris-Tröger’s base which has been submitted for its final characterizations. A specifically designed Tröger’s Base analogue was synthesized by functionalizing the benzylic position in the diazocine bridge, with (R)-menthyl ester groups, to make successful separation of previously enantiomeric Tröger’s base analogues possible. Tröger’s Base analogue, containing the bulkier ester side chain, was progressed through, to allow condensation to the tris-Tröger’s Base with a limited set of possible stereo-outcomes, and eventually the heptakis-Tröger’s Base. At the end of this project heptakis-Tröger’s Base is closer to
being successfully purified and characterized and its reaction intermediates has nearly been fully
characterized. (Less) - Popular Abstract
- The search for new breakthroughs is a never ending quest. No matter which field of science you look at there is always a new discovery around the corner, some envisioned and some stumbled upon. The focus of this thesis is one of the envisioned ones. Imagine if you could place the active substance of a pharmaceutical inside of a small vessel and transport it to a targeted part of a biological system. This would surely increase the potency of most existing drugs
on the market. As tool to accomplish this we had an interesting building block, discovered more than a century ago, Tröger’s base. Recent breakthroughs within the Tröger’s base chemistry had given us hope that maybe one day we would be able to utilize its v-shaped structure to... (More) - The search for new breakthroughs is a never ending quest. No matter which field of science you look at there is always a new discovery around the corner, some envisioned and some stumbled upon. The focus of this thesis is one of the envisioned ones. Imagine if you could place the active substance of a pharmaceutical inside of a small vessel and transport it to a targeted part of a biological system. This would surely increase the potency of most existing drugs
on the market. As tool to accomplish this we had an interesting building block, discovered more than a century ago, Tröger’s base. Recent breakthroughs within the Tröger’s base chemistry had given us hope that maybe one day we would be able to utilize its v-shaped structure to produce a small nano capsule. The focus of this thesis was to continue on this project, started by previous researcher within the group, investigate the possibility of forming these tubes. It was also to be considered what could be done with our molecule if nanotubes was not to be achieved, what other kinds of application we could find for our
structure? As a final part, importance was put into characterizing every intermediate building block along the way, and to improve on already existing chemistry. (Less)
Please use this url to cite or link to this publication:
http://lup.lub.lu.se/student-papers/record/8991376
- author
- Sjörén, Aleksander LU
- supervisor
- organization
- course
- KEMR31 20191
- year
- 2019
- type
- H2 - Master's Degree (Two Years)
- subject
- keywords
- Organic chemistry, Tröger's base, Diazocine bridge
- language
- English
- id
- 8991376
- date added to LUP
- 2023-06-28 15:24:18
- date last changed
- 2023-06-28 15:24:18
@misc{8991376,
abstract = {{The route towards linearly fused heptakis-Tröger’s base was followed using a 12 step synthesis route. Hope remains that the final compound will be purified to a satisfactory level within the near future. Additionally, characterizations of reaction intermediates has been completed, up to monoprotected tris-Tröger’s base which has been submitted for its final characterizations. A specifically designed Tröger’s Base analogue was synthesized by functionalizing the benzylic position in the diazocine bridge, with (R)-menthyl ester groups, to make successful separation of previously enantiomeric Tröger’s base analogues possible. Tröger’s Base analogue, containing the bulkier ester side chain, was progressed through, to allow condensation to the tris-Tröger’s Base with a limited set of possible stereo-outcomes, and eventually the heptakis-Tröger’s Base. At the end of this project heptakis-Tröger’s Base is closer to
being successfully purified and characterized and its reaction intermediates has nearly been fully
characterized.}},
author = {{Sjörén, Aleksander}},
language = {{eng}},
note = {{Student Paper}},
title = {{Improving the synthetic route towards linearly fused Tröger’s base analogues}},
year = {{2019}},
}