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Total synthesis of Mycestericin E:
Reference: Iwabuchi, Y.; Furukawa, M.; Esumi, T.; Hatakeyama, S. Chem. Commun. 2001, 2030. DOI
Keywords: CarboxEster → Alkyl-OH • O-H → O-SiPh2tBu • Alkyl-OH → Aldehyde-α-NR2 • Pinnick oxidation • Aldehyde → CarboxAcid • O-SiPh2tBu → O-H • Ketal → Ketone • N-C(O)OR → N-H • Epoxidation, nucleophilic EnoateEster • Ritter - epoxide • Li/H → Li-Dithiane • Li/H → Li-Alkynyl • Ketal(thio) → Ketone • O-SiMe2tBu → O-H • Ketone → Ketal • Alkyl-OH → Aldehyde • Li-Dithiane+Alkyl-X • Alkyl-X+Li-R • Li-Alkynyl+Alkyl-X • Alkyl-X+Li-R • Alkyne → Ene-trans • Morita-Bayliss-Hillman(asym) •
Reagents: NaOMe • Hydroperoxide, tbutyl • BH4-Na+ • SiPh2tBu-Cl • DBU • DMSO, (COCl)2 (Swern) • Chlorite, sodium • Diazomethane • BF3·OEt2 • HF • Hydroxide, sodium • Chiral catalyst • Acetonitrile, trichloro • Epoxide • BuLi(n) • Alkynyl-Li • MeI • TsOH • AlH4-Li+ • DMSO, (COCl)2 (Swern) • DMF (solvent) • Acrylate •

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