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978-3-8439-1684-4, Reihe Organische Chemie

Céline Joie
The Asymmetric Organocatalytic Aza-Michael Addition: Efforts towards the Total Synthesis of Yuremamine and Development of New Domino Reactions

155 Seiten, Dissertation Rheinisch-Westfälische Technische Hochschule Aachen (2014), Softcover, A5

Zusammenfassung / Abstract

This work first described the efforts made towards the total synthesis of yuremamine employing as key step an aza-Michael/aldol condensation domino sequence of a indole-2-carbaldehyde derivative and an alpha,beta-unsaturated aldehyde.

In the second project of this work, a new methodology for the synthesis of chiral tetracyclic pyridocarbazoles derivatives bearing six stereocentres was developed. The domino reaction established proceeds via a Diels-Alder/ aza-Michael/ aldol condensation sequence of 3-vinylindoles with 2 equivalents of alpha,beta-unsaturated aldehyde.

Continuing with the strategy exploited within this work, various substrates containing both a nucleophilic nitrogen atom and a Michael acceptor, which would allow a further cyclization of the aza-Michael addition product, can be designed.