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Rhodium-Catalyzed Endo-Selective Epoxide-Opening Cascades: Formal Synthesis of (−)-Brevisin

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journal contribution
posted on 03.06.2015, 00:00 by Kurt W. Armbrust, Matthew G. Beaver, Timothy F. Jamison
[Rh­(CO)2Cl]2 is as an effective catalyst for endo-selective cyclizations and cascades of epoxy-(E)-enoate alcohols, thus enabling the synthesis of oxepanes and oxepane-containing polyethers from di- and trisubstituted epoxides. Syntheses of the ABC and EF ring systems of (−)-brevisin via all endo-diepoxide-opening cascades using this method constitute a formal total synthesis and demonstrate the utility of this methodology in the context of the synthesis of marine ladder polyether natural products.

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