Facile synthesis and mechanistic investigations of bicyclic oxo-gamma-lactams from simple caprolactams

Weck, Christian and Nauha, Elisa and Gruber, Tobias (2018) Facile synthesis and mechanistic investigations of bicyclic oxo-gamma-lactams from simple caprolactams. In: ORCHEM, 10th-12th September 2018, Berlin.

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Item Type:Conference or Workshop contribution (Poster)
Item Status:Live Archive

Abstract

The 6-azabicyclo[3.2.1]octane has been of great interest for medicinal chemists for some time now. Several natural products with a wide variety of different properties have been isolated and characterized such as Aphanorphine, Actinobolamine, Peduncularine or Lyconadin A.
Here we describe the preparation of the Avibactam related 6-azabicyclo[3.2.1]octane bridged ring system, starting from a readily available caprolactam precursor. This straightforward approach consists of a Dieckmann-cyclization with an ester group in C-6 position. The cyclization results in an oxo-gamma-lactam system, which is believed to show
enhanced reactivity towards nucleophilic ring opening.

Keywords:lactam, Dieckmann cyclization, heterocycle
Subjects:F Physical Sciences > F160 Organic Chemistry
F Physical Sciences > F151 Pharmaceutical Chemistry
Divisions:College of Science > School of Pharmacy
ID Code:34800
Deposited On:25 Jan 2019 16:29

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