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Issue 19, 2012
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Stereoselective synthesis of functionalised carbocyclic amides: construction of the syn-(4aS,10bS)-phenanthridone skeleton

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Abstract

A new synthetic approach has been developed for the preparation of 7-deoxypancratistatin analogues bearing a syn-(4aS,10bS)-phenanthridone ring junction. A one-pot tandem process involving a substrate-directed Overman rearrangement and ring closing metathesis reaction was developed for the stereoselective synthesis of a carbocyclic allylic trichloroacetamide. Conversion to a 6-bromopiperonyl amide, followed by a Heck reaction generated a homoallylic alcohol and completed the syn-(4aS,10bS)-phenanthridone carbon skeleton. Stereoselective epoxidation and dihydroxylation of the syn-(4aS,10bS)-phenanthridone framework was then investigated leading to the preparation of new analogues of 7-deoxypancratistatin.

Graphical abstract: Stereoselective synthesis of functionalised carbocyclic amides: construction of the syn-(4aS,10bS)-phenanthridone skeleton

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Publication details

The article was received on 15 Feb 2012, accepted on 16 Mar 2012 and first published on 19 Mar 2012


Article type: Paper
DOI: 10.1039/C2OB25334H
Citation: Org. Biomol. Chem., 2012,10, 3937-3945
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    Stereoselective synthesis of functionalised carbocyclic amides: construction of the syn-(4aS,10bS)-phenanthridone skeleton

    S. Ahmad, M. D. Swift, L. J. Farrugia, H. M. Senn and A. Sutherland, Org. Biomol. Chem., 2012, 10, 3937
    DOI: 10.1039/C2OB25334H

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