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A chemoenzymatic total synthesis of the Amaryllidaceae alkaloid narseronine

Schwartz, Brett; Banwell, Martin; Cade, Ian

Description

A 15-step and fully stereocontrolled total synthesis of the title alkaloid 1 has been accomplished using the enantiomerically pure and enzymatically- derived cis-1,2-dihydrocatechol 2 as starting material. The final and pivotal step involved the intramolecular hetero-Michael addition of secondary amine 16 to a tethered enone moiety followed by trapping of the resulting enolate through its reaction with an adjacent ester residue.

CollectionsANU Research Publications
Date published: 2011
Type: Journal article
URI: http://hdl.handle.net/1885/59252
Source: Tetrahedron Letters
DOI: 10.1016/j.tetlet.2011.06.050

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