Studies toward the Total Synthesis of Axinellamine and Massadine
- 1 September 2007
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (20), 3861-3864
- https://doi.org/10.1021/ol0711568
Abstract
Intramolecular Diels−Alder reactions of several N−O linked 4-vinylimidazole dimers provide the expected adduct in moderate to good yield as a single, all trans stereoisomer, along with smaller amounts of the inverse electron demand adduct. Oxidative rearrangement of the cycloadducts occurs on treatment with Davis' reagent, providing a single spiro imidazolone in good yield and with excellent levels of stereocontrol albeit epimeric at the spiro center found in axinellamine and massadine.Keywords
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