Formal total synthesis of (+)-diepoxin sigma |
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Authors: | Wipf P Jung J K |
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Institution: | Department of Chemistry, University of Pittsburgh, Pennsylvania 15260, USA. pwipf+@pitt.edu |
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Abstract: | The highly oxygenated antifungal anticancer natural product (+/-)-diepoxin sigma was prepared in 10 steps and in 15% overall yield from O-methylnaphthazarin. Highlights of the synthetic work include an Ullmann coupling and a possibly biomimetic oxidative spirocyclization for the introduction of the naphthalene ketal as well as the use of a retro-Diels-Alder reaction to unmask the reactive enone moiety in the naphthoquinone bisepoxide ring system. A novel highly bulky chiral binaphthol ligand was developed for a boron-mediated Diels-Alder reaction that constitutes a formal asymmetric total synthesis of (+)-diepoxin sigma. |
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