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Assignment of absolute configuration to SCH 351448 via total synthesis.

ABSTRACT: The synthesis and absolute configuration of SCH 351448, an interesting ionophoric natural product, are reported herein. Mukaiyama aldol-Prins and segment-coupling Prins reactions were employed to construct the constituent tetrahydropyrans of SCH 351448. Efforts to assemble the C2-symmetric core of the natural product by a templated olefin metathesis strategy are described; however, a stepwise fragment assembly was ultimately utilized to complete the target molecule.

SUBMITTER: Cheung LL

PROVIDER: S-EPMC2574719 | biostudies-literature | 2008 Jul

REPOSITORIES: biostudies-literature

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Assignment of absolute configuration to SCH 351448 via total synthesis.

Cheung Lael L LL Marumoto Shinji S Anderson Christopher D CD Rychnovsky Scott D SD

Organic letters 20080611 14

The synthesis and absolute configuration of SCH 351448, an interesting ionophoric natural product, are reported herein. Mukaiyama aldol-Prins and segment-coupling Prins reactions were employed to construct the constituent tetrahydropyrans of SCH 351448. Efforts to assemble the C2-symmetric core of the natural product by a templated olefin metathesis strategy are described; however, a stepwise fragment assembly was ultimately utilized to complete the target molecule. ...[more]

PMID: 18543942

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