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Rhodium-catalyzed endo-selective epoxide-opening cascades: formal synthesis of (-)-brevisin.

ABSTRACT: [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.

SUBMITTER: Armbrust KW

PROVIDER: S-EPMC4586266 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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Rhodium-catalyzed endo-selective epoxide-opening cascades: formal synthesis of (-)-brevisin.

Armbrust Kurt W KW Beaver Matthew G MG Jamison Timothy F TF

Journal of the American Chemical Society 20150518 21

[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 produc ...[more]

PMID: 25984951

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