Synthetic steps towards the cylindrospermopsin alkaloids
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Abstract
Detailed herein is the tethered Biginelli condensation between iminium ion
201 and β-keto ester 206 leading to a model tricyclic ring system representative of the guanidinium core of cylindrospermopsin alkaloids. This was achieved in a
biosynthetically-inspired manner in 12 steps and 8.3% overall yield from simple,
commercially available 1,5-pentanediol 172. Also discussed is the adaption of this
methodology to allow for the highly efficient stereoselective synthesis of all 3 of the
cylindrospermopsin alkaloids and the preparation of the advanced synthetic
intermediate nitro-alcohol 223.
201 and β-keto ester 206 leading to a model tricyclic ring system representative of the guanidinium core of cylindrospermopsin alkaloids. This was achieved in a
biosynthetically-inspired manner in 12 steps and 8.3% overall yield from simple,
commercially available 1,5-pentanediol 172. Also discussed is the adaption of this
methodology to allow for the highly efficient stereoselective synthesis of all 3 of the
cylindrospermopsin alkaloids and the preparation of the advanced synthetic
intermediate nitro-alcohol 223.
Details
| Original language | English |
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| Awarding Institution |
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| Supervisors/Advisors |
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| Award date | Nov 2012 |