Total Synthesis of the Spliceosome Modulator Pladienolide B via Asymmetric Alcohol‐Mediated <i>syn</i>‐ and <i>anti</i>‐Diastereoselective Carbonyl Crotylation

Yoo, Minjin; Krische, Michael J.

doi:10.1002/ange.202103845

Angewandte Chemie

2021

DOI: 10.1002/ange.202103845

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Total Synthesis of the Spliceosome Modulator Pladienolide B via Asymmetric Alcohol‐Mediated syn‐ and anti‐Diastereoselective Carbonyl Crotylation

Minjin Yoo

Michael J. Krische

Abstract: The potent spliceosome modulator pladienolide B, which bears 10 stereogenic centers, is prepared in 10 steps (LLS). Asymmetric alcohol‐mediated carbonyl crotylations catalyzed by ruthenium and iridium that occur with syn‐ and anti‐diastereoselectivity, respectively, were used to form the C20‐C21 and C10‐C11 C−C bonds.

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Stereo‐ and Site‐Selective Crotylation of Alcohol Proelectrophiles via Ruthenium‐Catalyzed Hydrogen Auto‐Transfer Mediated by Methylallene and Butadiene

et al. 2022

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Iodide-bound ruthenium-JOSIPHOS complexes catalyze the redox-neutral CÀ C coupling of primary alcohols with methylallene (1,2-butadiene) or 1,3-butadiene to form products of anti-crotylation with good to excellent levels of diastereo-and enantioselectivity. Distinct from other methods, direct crotylation of primary alcohols in the presence of unprotected secondary alcohols is possible, enabling generation of spirastrellolide B (C9-C15) and leucascandrolide A (C9-C15) substructures in significantly fewer steps than previously possible.

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Stereo‐ and Site‐Selective Crotylation of Alcohol Proelectrophiles via Ruthenium‐Catalyzed Hydrogen Auto‐Transfer Mediated by Methylallene and Butadiene

et al. 2022

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Stereo‐ and Site‐Selective Crotylation of Alcohol Proelectrophiles via Ruthenium‐Catalyzed Hydrogen Auto‐Transfer Mediated by Methylallene and Butadiene

et al. 2022

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Total Synthesis of the Spliceosome Modulator Pladienolide B via Asymmetric Alcohol‐Mediated syn‐ and anti‐Diastereoselective Carbonyl Crotylation

Cited by 2 publications

References 52 publications

Stereo‐ and Site‐Selective Crotylation of Alcohol Proelectrophiles via Ruthenium‐Catalyzed Hydrogen Auto‐Transfer Mediated by Methylallene and Butadiene

Stereo‐ and Site‐Selective Crotylation of Alcohol Proelectrophiles via Ruthenium‐Catalyzed Hydrogen Auto‐Transfer Mediated by Methylallene and Butadiene

Stereo‐ and Site‐Selective Crotylation of Alcohol Proelectrophiles via Ruthenium‐Catalyzed Hydrogen Auto‐Transfer Mediated by Methylallene and Butadiene

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