Total synthesis of Japonilure:
| Reference: | Papillon, J. P. N.; Taylor, R. J. K. Org. Lett. 2002, 4, 119. DOI |
| Reactions: | O-C(O)NR2 → O-H • Alkyne → Ene-cis (Lindlar) • Ozonolysis • CompOx-Alkene/Alkyne+O3 • Li-R → Zn-R • Li/H → Li-Ether (asym) • Cu-Alkyl+Alkynyl-Br • Alkynyl-Br+Cu-R • O-C(O)NR2 → O-H • Lactol → Lactone • Lactone-5 • O-H → O-C(O)NR2 • |
| Reagents: | NaH • O=C(NR2)Cl • Sulfonic acid, methane • Hydroxide, barium • O3 • PPh3 • I2 • H2, Pd • BuLi, Sparteine • ZnCl2 • CuCN • Alkynyl-Br • Chiral catalyst (misc) • |