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Synthetic steps towards the cylindrospermopsin alkaloids

Authors
  • Evans, Daniel Mackenzie
Publication Date
Jan 01, 2012
Source
OpenGrey Repository
Keywords
Language
English
License
Unknown

Abstract

Detailed herein is the tethered Biginelli condensation between irninium ion 201 and beta keto ester 206 leading to a model tricyclic ring system representative of the guanidinium core of cylindrospennopsin 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. / EThOS - Electronic Theses Online Service / GB / United Kingdom

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