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Total synthesis of ramonanins A-D.

Authors :
Harvey RS
Mackay EG
Roger L
Paddon-Row MN
Sherburn MS
Lawrence AL
Source :
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2015 Feb 02; Vol. 54 (6), pp. 1795-8. Date of Electronic Publication: 2014 Dec 15.
Publication Year :
2015

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.<br /> (© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Details

Language :
English
ISSN :
1521-3773
Volume :
54
Issue :
6
Database :
MEDLINE
Journal :
Angewandte Chemie (International ed. in English)
Publication Type :
Academic Journal
Accession number :
25510556
Full Text :
https://doi.org/10.1002/anie.201409818