Total Synthesis of the Spliceosome Modulator Pladienolide B via Asymmetric Alcohol‐Mediated <i>syn</i> ‐ and <i>anti</i> ‐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.
Topics & Concepts
SpliceosomeAlcoholChemistryStereochemistryOrganic chemistryBiochemistryRNA splicingGeneRNASynthetic Organic Chemistry MethodsChemical Synthesis and AnalysisMicrobial Natural Products and Biosynthesis