Total Synthesis of Ramonanins A–D

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

Research output: Contribution to journalArticlepeer-review

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.
Original languageEnglish
Pages (from-to)1795-1798
Number of pages4
JournalAngewandte Chemie International Edition
Volume54
Issue number6
Early online date15 Dec 2014
DOIs
Publication statusPublished - 2 Feb 2015

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