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Synthesis of the tetracyclic core of exiguaquinol.

ABSTRACT: A Diels-Alder reaction, a desymmetrizing aldol reaction, and a reductive Heck cyclization are employed in a short synthesis of a tetracycle relevant to exiguaquinol, a potential antibiotic. Ground-state energies of this advanced model system and the natural product rationalize the incorrect hemiaminal configuration experimentally obtained and point to the importance of the sulfonate in dictating the relative configuration of the natural product.

SUBMITTER: Schwarzwalder GM

PROVIDER: S-EPMC3946388 | biostudies-literature | 2013 Dec

REPOSITORIES: biostudies-literature

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Synthesis of the tetracyclic core of exiguaquinol.

Schwarzwalder Gregg M GM Steinhardt Sarah E SE Pham Hung V HV Houk K N KN Vanderwal Christopher D CD

Organic letters 20131112 23

A Diels-Alder reaction, a desymmetrizing aldol reaction, and a reductive Heck cyclization are employed in a short synthesis of a tetracycle relevant to exiguaquinol, a potential antibiotic. Ground-state energies of this advanced model system and the natural product rationalize the incorrect hemiaminal configuration experimentally obtained and point to the importance of the sulfonate in dictating the relative configuration of the natural product. ...[more]

PMID: 24219829

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