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Formal synthesis of (-)-kendomycin featuring a Prins-cyclization to construct the macrocycle.

ABSTRACT: The kendomycin skeleton was prepared by a highly convergent strategy in which the benzofuran fragment and the acyclic iodide fragment were prepared by standard methods and joined using a Suzuki coupling. The distinctive reaction in our approach was an intramolecular Prins cyclization that assembles the macrocyclic ring in good yield. Modeling studies demonstrate that the acyclic chain is predisposed for macrocycle formation. Ultimately, the product was correlated with one of Lee's advanced intermediates for a formal total synthesis of kendomycin.

SUBMITTER: Bahnck KB

PROVIDER: S-EPMC2697922 | biostudies-literature | 2008 Oct

REPOSITORIES: biostudies-literature

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Formal synthesis of (-)-kendomycin featuring a Prins-cyclization to construct the macrocycle.

Bahnck Kevin B KB Rychnovsky Scott D SD

Journal of the American Chemical Society 20080904 39

The kendomycin skeleton was prepared by a highly convergent strategy in which the benzofuran fragment and the acyclic iodide fragment were prepared by standard methods and joined using a Suzuki coupling. The distinctive reaction in our approach was an intramolecular Prins cyclization that assembles the macrocyclic ring in good yield. Modeling studies demonstrate that the acyclic chain is predisposed for macrocycle formation. Ultimately, the product was correlated with one of Lee's advanced inter ...[more]

PMID: 18767844

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