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Total synthesis of aspeverin via an iodine(III)-mediated oxidative cyclization.

ABSTRACT: The first total synthesis of aspeverin, a prenylated indole alkaloid isolated from Aspergillus versicolor in 2013, is described. Key steps utilized to assemble the core structure of the target include a highly diastereoselective Diels-Alder reaction, a Curtius rearrangement, and a unique strategy for installation of the geminal dimethyl group. A novel iodine(III)-initiated cyclization was then used to install the bicyclic urethane linkage distinctive to the natural product.

SUBMITTER: Levinson AM

PROVIDER: S-EPMC5633934 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature

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Total synthesis of aspeverin via an iodine(III)-mediated oxidative cyclization.

Levinson Adam M AM

Organic letters 20140829 18

The first total synthesis of aspeverin, a prenylated indole alkaloid isolated from Aspergillus versicolor in 2013, is described. Key steps utilized to assemble the core structure of the target include a highly diastereoselective Diels-Alder reaction, a Curtius rearrangement, and a unique strategy for installation of the geminal dimethyl group. A novel iodine(III)-initiated cyclization was then used to install the bicyclic urethane linkage distinctive to the natural product. ...[more]

PMID: 25171639

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