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Total synthesis of ramonanins A-D

Harvey, Ross S; Mackay, Emily G; Roger, Lukas; Paddon-Row, Michael N; Sherburn, Michael; Lawrence, Andrew L.

Description

The first total synthesis of the ramonanin family of lignan natural products is described. The short synthesis involves a 2,5-diaryl-3,4-dimethylene tetrahydrofuran intermediate, which participates in an unexpectedly facile Diels-Alder dimerization, generating all four natural products. Insights into the reactivity and stereoselectivity of the key dimerization are provided through computational studies employing B3LYP/6-31G(d) and M06-2X/6-31G(d) model chemistries.

CollectionsANU Research Publications
Date published: 2015-02-02
Type: Journal article
URI: http://hdl.handle.net/1885/13592
Source: Angewandte Chemie International Edition
DOI: 10.1002/anie.201409818

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