Total synthesis of Pseudopterosin:
| Reference: | Newton, C. G.; Drew, S. L.; Lawrence, A. L.; Willis, A. C.; Paddon-Row, M. L.; Sherburn, M. S. Nature Chem. 2015, 7, 82–86. DOI |
| Reactions: | Nef reaction • Alkyl-NO2 → Ketone • Diels-Alder, Enal • Bicyclo(440) • Diels-Alder, Enal • Diels-Alder, Allene • Diels-Alder, EneNitro • Bicyclo(440) • Wittig-isopropyl • Pd/H-Alkynyl+Vinyl-X • Pd/Mg-Vinyl+Propargyl-X • Decarbonylation • C-C(O)H → C-H • Ketone → Ketone-α-OR • Oxaziridine+Enolate • Ketone-α-OR → Ketone-1,2-di • Ketone-1,2-di • O-H → O-SO2Me • CarboxEster → Aldehyde • Benzene synthesis • |
| Reagents: | Vinyl-Br • Sulfonyl chloride, methane, NEt3 • Ni(dppp)Cl2 • PPh3 • Propenyl-MgX • Acrolein • Rh(PPh3)3Cl • AlHiBu2 • PPh3=CMe2 • EneNitro • KOtBu • KN(SiMe3)2 • Oxaziridine • DMSO, (COCl)2 (Swern) • Pd(PPh3)4 • CuI • Dioxirane • BuLi(n) • |