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Total synthesis of Cerulenin (Townsend):
Reference: Mani, N. S.; Townsend, C. A. J. Org. Chem. 1997, 62, 636. DOI
Keywords: O-H → O-Ethoxyethyl • Li-Epoxide+Aldehyde • Aldehyde+Li-R • Sharpless epoxidation • Si-Oxiranyl → H-Oxiranyl • Lactone → CarboxAmide • CompE+-Lactone/Epoxide+NH3 • Li/H → Li-Epoxide • Alkyl-OH → Aldehyde-α-OR • Lactone-5 • O-Ethoxyethyl → O-H • Alkyl-OH → Ketone-α-OR •
Reagents: Vinyl-SiR3 • Epoxide • Vinyl-OR • BuLi(sec), TMEDA • Fluoride, R4N+ • TsOH·Py • RuO4-Pr4N+, NMO • NH3 • RuO4-Pr4N+, NMO • Ti(OEt)4

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