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Total synthesis of Punctatin A:
Reference: Paquette, L. A.; Sugomura, T. J. Am. Chem. Soc. 1987, 109, 3017. DOI
Keywords: Enone → Allyl-OH • O-H → O-Alkyl • Williamson etherification • Hydroboration alkene • Alkyl-OH → Ketone • O-SEM → O-H • Alkyl-OH → Ketone • Ketone → EnolSilane • Saegusa oxidation • Ketone → Enone • Enone → Allyl-OH • O-SiMe3 → O-H • O-MOM → O-H • O-C(O)R → O-H • Enone enolate+Alkyl-X • Alkyl-X+Enolate • Li/Sn → Li-Ether • Ketone epimerization • Mitsunobu → Ester • Allyl-OH → Allyl-OAc • Photochemistry • Li/Sn → Li-Ether • 2,3-Sigmatropic Anionic • O-H → O-MEM •
Reagents: NaH • AlH4-Li+ • SnBu3-CH2-I • BH3·THF • 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 • DMSO (solvent) • BuLi(n) • H2O2, NaOH •

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