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ISBN 9783843927390

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978-3-8439-2739-0, Reihe Organische Chemie

Stephanie Ganß
Intramolecular Rhodium-Catalyzed Hydro-Oxycarbonylation of Alkynes and Allenes: New Asymmetric Access to Vinylic Macrolactones

378 Seiten, Dissertation Albert-Ludwigs-Universität Freiburg im Breisgau (2016), Softcover, A5

Zusammenfassung / Abstract

Macrocyclic natural products are captivating owing to their often complex molecular architecture of a large ring combined with a broad diversity of functional groups and high stereochemical complexity. In particular, macrocyclic scaffolds of the macrolactone family are present in numerous natural compounds exhibiting intriguing fungicidal and insecticidal bioactivity, as well as olfactory and medicinal properties.

This dissertation describes the development of an intramolecular rhodium-catalyzed hydro-oxycarbonylation of omega-allenyl-substituted carboxylic acids. This process represents a new atom-economical and asymmetric macrolactone formation avoiding the need for stoichiometric activating reagents and preceding installation of the stereoinformation. The macrolactonization proceeds with good to high enantio- and diastereoselectivity and displays a broad functional group tolerance.