Total Synthesis of Ramonanins A–D |
| |
| Authors: | Ross S. Harvey Emily G. Mackay Lukas Roger Prof. Michael N. Paddon‐Row Prof. Michael S. Sherburn Dr. Andrew L. Lawrence |
| |
| Affiliation: | 1. Research School of Chemistry, Australian National University, Canberra, ACT 2601 (Australia);2. School of Chemistry, The University of New South Wales, Sydney, NSW 2052 (Australia);3. School of Chemistry, The University of Edinburgh, Joseph Black Building, West Mains Road, Edinburgh, EH9 3JJ (UK) |
| |
| 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. |
| |
| Keywords: | biomimetic synthesis Diels– Alder reactions enyne metathesis lignans natural products |
|
|
