Total synthesis of Punctatin A:
| Reference: | Paquette, L. A.; Sugomura, T. J. Am. Chem. Soc. 1987, 109, 3017. DOI |
| Reactions: | Enone → Allyl-OH • O-H → O-Alkyl • Williamson etherification • Enone enolate+Alkyl-X • Alkyl-X+Enolate • Li/Sn → Li-Ether • Li/Sn → Li-Ether • 2,3-Sigmatropic Anionic • O-H → O-MEM • Hydroboration → Alkyl-OH • O-SEM → O-H • Ketone epimerization • Photochemistry • Cyclobutane • Bicyclo(420) • Alkyl-OH → Ketone • Alkyl-OH → Ketone • Saegusa oxidation • Ketone → Enone • Enone → Allyl-OH • Ketone → EnolSilane • O-SiMe3 → O-H • O-MOM → O-H • O-C(O)R → O-H • Mitsunobu → OC(O)R • Allyl-OH → Allyl-OC(O)R • Alkyl-OH inversion • |
| Reagents: | NaH • AlH4-Li+ • SnBu3-CH2-I • DMSO (solvent) • BuLi(n) • BH3·THF • H2O2, NaOH • MEM-Cl • CrO3Cl·PyH (PCC) • NaOMe • Photochemistry • Fluoride, R4N+ • CrO3Cl·PyH (PCC) • SiMe3-CH2CO2Me • Fluoride, R4N+ • Pd(OAc)2 • AlHiBu2 • PPh3, DEAD • Benzoic acid • HClO4 • Hydroxide, sodium • |