Synthetic steps towards the cylindrospermopsin alkaloids

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.

Date of Award	Nov 2012
Original language	English
Awarding Institution	Bangor University
Supervisor	Paddy Murphy (Supervisor)