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

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.

Automated summary

This research synthesized the potent spliceosome modulator pladienolide B with 10 stereogenic centers in 10 steps. Asymmetric alcohol-mediated carbonyl crotylations catalyzed by ruthenium and iridium were used to form the C20-C21 and C10-C11 C-C bonds with syn- and anti-diastereoselectivity, respectively.