image

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-Tr -> 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 • Allyl-OH -> Allyl-OSO2R • Ketone enolate+Alkyl-X • 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 • Ag2CO3 • I2

Syntheses Home