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Total synthesis of Roflamycoin (Part 2):
Reference: Rychnovsky, S. D.; Khire, U. R.; Yang, G. J. Am. Chem. Soc. 1997, 119, 2058. DOI (Part 3) (Part 1)
Keywords: O-SiMe2tBu → O-H • Alkyl-OH → Alkyl-I • Li-Nitrile+Alkyl-X • Alkyl-X+Enolate • Alkyl-OH → Aldehyde • Ketal → Diol-1,2 • Alkyl-C≡N → Alkyl-H • O-Bn → O-H • Li-Nitrile+Alkyl-X • Alkyl-X+Enolate • EnolEther → Enal • HWE → EnoateEster • Diol-1,2 cleavage • Li/Sn → Li-Vinyl • Li-Vinyl → Mg-Vinyl • Aldehyde+Li-Vinyl • Li-Vinyl+Aldehyde • CarboxAcid → CarboxEster •
Reagents: LiNEt2 • DMPU (solvent) • Fluoride, R4N+ • PPh3, I2 • LiNEt2 • DMPU (solvent) • Li°/NH3 • BOP • Dess-Martin • Sulfonyl chloride, methane, NEt3 • DBU • Dowex • Periodate, sodium • Butadiene, 1-SnR3 • Butadiene, 1-OR • BuLi(n) • MgBr2

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