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Total Synthesis of Ramonanins A–D
Author(s) -
Harvey Ross S.,
Mackay Emily G.,
Roger Lukas,
PaddonRow Michael N.,
Sherburn Michael S.,
Lawrence Andrew L.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201409818
Subject(s) - stereoselectivity , total synthesis , chemistry , reactivity (psychology) , tetrahydrofuran , lignan , stereochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology , solvent
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.