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Total synthesis of ramonanins A-D

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Date

2015-02-02

Authors

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

Journal Title

Journal ISSN

Volume Title

Publisher

Wiley

Abstract

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.

Description

Keywords

diels-alder reactions, biomimetic synthesis, enyne metathesis, lignans, natural products

Citation

URI

http://hdl.handle.net/1885/13592

Collections

ANU Research Publications

Source

Angewandte Chemie International Edition

Type

Journal article

Book Title

Entity type

Access Statement

License Rights

DOI

10.1002/anie.201409818

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