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Total synthesis of Japonilure:
Reference: Papillon, J. P. N.; Taylor, R. J. K. Org. Lett. 2002, 4, 119. DOI
Keywords: O-C(O)NR2 → O-H • Alkyne → Ene-cis (Lindlar) • Ozonolysis • CompOx-Alkene/Alkyne+O3 • Li-R → Zn-R • Li/H(asym) → Li-Ether • Li-R → Zn-R • 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 (amine) •

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