Synthesis of Diarylheptanoid Scaffolds Inspired by Calyxins I and J

doi:https://doi.org/10.1021/acs.orglett.5b01848

Open AccessArticle10.1021/acs.orglett.5b01848

Synthesis of Diarylheptanoid Scaffolds Inspired by Calyxins I and J

Thomas D. Ackrill,Hazel A. Sparkes,Christine L. Willis-2015-07-24-Organic Letters

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TL;DRAbstract

γ,δ-Unsaturated alcohols are prepared efficiently in two steps from o-hydroxycinnamaldehyde. The TMSOTf-mediated reaction of the γ,δ-unsaturated alcohols with aldehydes creates two oxygen heterocycles and three new stereocenters in a single pot. The approach is versatile, and by varying the boronic acid, Grignard reagent, and aldehyde, different substituents may be introduced, while use of a chiral base in the conjugate addition gives enantioenriched products.

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γ,δ-Unsaturated alcohols are prepared efficiently in two steps from o-hydroxycinnamaldehyde. The TMSOTf-mediated reaction of the γ,δ-unsaturated alcohols with aldehydes creates two oxygen heterocycles and three new stereocenters in a single pot. The approach is versatile, and by varying the boronic acid, Grignard reagent, and aldehyde, different substituents may be introduced, while use of a chiral base in the conjugate addition gives enantioenriched products.

Keywords

ChemistryCombinatorial chemistryStereochemistry

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