Total synthesis of Pareitropone:
| Reference: | Feldman, K. S.; Cutarelli, T. D. J. Am. Chem. Soc. 2002, 124, 11600. DOI |
| Reactions: | CarboxAcid → Alkyl-OH • Li/H → Li-Alkynyl • Mitsunobu → Amine • Alkyl-OH → Alkyl-NR2 • Li/H → Li-Aryl • Epoxide+Li-R • Li-Aryl+Epoxide • Li-Diazomethane+Aldehyde • Sn-Alkynyl → Alkynyl-iodonium • Aldehyde → Alkyne • Quinoline synthesis • Tropone synthesis • Carbene Cycloaddition • Mechanism • Mg-Aryl+Aryl-OMe • Alkynyliodonium • Amine-6 • Bicyclo(430)-aza • Iodonium • Cyclopentene • Carbene Cycloaddition • Mechanism • O-H → O-SiMe2tBu • CompNu-O-H/O-H+R3Si-X • Alkyl-OH → Aldehyde • O-SiPh2tBu → O-H • O-SiiPr3 → O-H • Lactone-6 • Li-R → Sn-R • |
| Reagents: | BuLi(n) • Epoxide • HCl, H2O • AlH4-Li+ • SiMe2tBu-Cl • Cr2O7·2PyH (PDC) • LiNiPr2 • HF • Alkynyl-Li • BuLi(n) • Alkynyl-SnR3 • Iodosobenzene-cyanotriflate • Fluoride, potassium • O2 • Diazomethane, silyl • PPh3, DEAD • SnBu3-Cl • LiN(SiMe3)2 • Aryl-MgX • Aryl-Li • |