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Total synthesis of Compactin:
Reference: Keck. G. E.; Kachensky, D. F. J. Org. Chem. 1986, 51, 2487. DOI
Keywords: O-H → O-Me • O-THP → O-H • O-CPh3 → O-H • O-H → O-SiMe2tBu • Ozonolysis • Ketone → Alkyl-OH • O-H → O-C(O)OR • O-SiMe2tBu → O-H • Lactol → Lactone • Li-Alkynyl+Aldehyde • Allene synthesis • O-H → O-SO2R • Ketone enolate+Alkyl-X • Alkyl-X+Enolate • Wittig-ketomethyl → Enone • Diels-Alder, Allene • Furst-Plattner diaxial • Epoxide reduction • Radical alkylation (Keck) Sn-Allyl •
Reagents: Alkynyl-Li • MeI • TsOH·Py • AlH4-Li+ • I2 • BuLi(n) • TsCl • PPh3 • Cooke dianion • NaH • SO2 • AlH4-Li+ • Li°/NH3 • S=C(OPh)Cl • Allyl-SnR3 • Photochemistry • SiPh2tBu-Cl • HCl, H2O • Ag2CO3 • I2

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