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Modular access to complex prodiginines: total synthesis of (+)-roseophilin via its 2-azafulvene prototropisomer.

ABSTRACT: Ansa-bridged prodiginines are bioactive pigments produced by bacteria. Certain of these structures are reported to be antagonists of protein-protein interactions involved in apoptosis. We describe a new entry to alkaloids of this type, demonstrated with a concise asymmetric synthesis of (+)-roseophilin (3). Our route constructs the pyrrolophane motif via phosphoryl transfer-terminated macroaldolization and passes through a previously unexplored prototropic form of the natural product.

SUBMITTER: Frederich JH

PROVIDER: S-EPMC3675760 | biostudies-literature | 2013 Mar

REPOSITORIES: biostudies-literature

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Modular access to complex prodiginines: total synthesis of (+)-roseophilin via its 2-azafulvene prototropisomer.

Frederich James H JH Harran Patrick G PG

Journal of the American Chemical Society 20130301 10

Ansa-bridged prodiginines are bioactive pigments produced by bacteria. Certain of these structures are reported to be antagonists of protein-protein interactions involved in apoptosis. We describe a new entry to alkaloids of this type, demonstrated with a concise asymmetric synthesis of (+)-roseophilin (3). Our route constructs the pyrrolophane motif via phosphoryl transfer-terminated macroaldolization and passes through a previously unexplored prototropic form of the natural product. ...[more]

PMID: 23452332

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