Total synthesis of Rhodomollein XX (Part 2) New:
| Reference: | Yu, K.; Yang, Z.-N.; Liu, C.-H.; Wu, S.-Q.; Hong, X.; Zhao, X.-L.; Ding, H. J. Am. Chem. Soc. 2019, 58, 8556-8560. DOI (Part 1) |
| Reactions: | Ketone-α-OR → Ketone • Epoxidation, dioxirane • Radical rearrangement • Epoxide reduction • Cyclopentanone • Bicyclo(321) • Petasis reagent • Ketone → C=CH2 • CompE-Ketone/Ketone+M-R • Ketal → Ketone • Ketone → Enone • Alkene hydration • Enone → EnolSilane • O-H → O-SiMe2tBu • CompNu-O-H/O-H+R3Si-X • Mg-Alkyl+Ketone • EnolSilane → Ketone-α-OH • Ketone → Ketone-α-OR • O-SiMe2tBu → O-H • Rubottom oxidation • |
| Reagents: | SmI2 • TiCp2Cl2 • TiCp2Me2 (Petasis) • TsOH • SePh-Cl • HSiPhH2 • O2 • SiMe2tBu-OTf • NEt3 • Me-MgBr • ReMeO3 • H2O2 • Pyridine • TsOH·Py • Dioxirane • |