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Total synthesis of Dactylolide:
Reference: Louis, I.; Hungerford, N. L.; Humphries, E. J.; McLeod, M. D. Org. Lett. 2006, 8, 1117. DOI
Keywords: O-SiEt3 -> O-H • O-PMB -> O-H • Alkyl-OH -> Aldehyde • Wittig-methyl • O-SiMe2tBu -> O-H • Alkyl-OH -> Aldehyde • Li/Br -> Li-Vinyl • Li-Vinyl -> Mg-Vinyl • O-H -> O-C(O)R • CarboxAcid -> Alkyl-OH • O-H -> O-SiMe2tBu • O-PMB -> O-H • Lactone -> Lactol • Alkyl-OH -> Aldehyde • Mg-Vinyl -> Ce-Vinyl • O-H -> O-SiMe2tBu • CarboxAcid -> CarboxEster • Mitsunobu -> Ester • Alkyl-OH -> Alkyl-OC(O)R • O-SiMe2tBu -> O-H • Alkyl-OH -> Aldehyde • Alkyl-OH -> Ketone • Diels-Alder, Aldehyde • Li-Vinyl+Aldehyde • Felkin-Anh Chelation • Claisen-Ireland • RCM -> Lactone • Wittig-carboxymethyl -> EnoateEster • Ce-Vinyl+Aldehyde • Aldehyde+Ce-R • RCM -> Lactone •
Reagents: Chiral catalyst • Fluoride, Bu4N+ • DDQ • DMSO, Py·SO3 • PPh3=CH2 • Fluoride, Bu4N+ • DMSO, Py·SO3 • NEt3 • BuLi(tert) • MgBr2 • NEt3 • LiN(SiMe3)2 • SiMe3-Cl • HCl • AlH4-Li+ • NEt3 • DDQ • Grubbs II • AlHiBu2 • Formate, methyl • Dess-Martin • Vinyl-MgX • CeCl3 • SiMe2tBu-Cl • Hydroxide, sodium • PPh3, DEAD • HCl • Dess-Martin •

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