| 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 |