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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-PMB → O-H • O-SiMe2tBu → O-H • Alkyl-OH → Aldehyde • Li/Br → Li-Vinyl • Li-R → Mg-R • O-PMB → O-H • Lactone → Lactol • Alkyl-OH → Aldehyde • Mg-R → Ce-R • O-H → O-SiMe2tBu • CarboxEster → CarboxAcid • O-SiMe2tBu → O-H • Diels-Alder, Aldehyde • Mg-Vinyl+Aldehyde • Felkin-Anh Chelation • Claisen-Ireland • RCM → Lactone • Lactone-6 • Wittig-carboxymethyl → EnoateEster • Ce-Vinyl+Aldehyde • Aldehyde+Ce-R • CompE+-Aldehyde/CarboxEster+M-R • RCM → Lactone • Lactone-9+ • CarboxAcid → Alkyl-OH • Wittig-methyl • Alkyl-OH → Aldehyde • EnolSilane → Ketone • O-H → O-C(O)R • Mitsunobu → Ester • CarboxAcid → CarboxEster • Alkyl-OH → Alkyl-OC(O)R • Alkyl-OH → Aldehyde • Allyl-OH → Enone • O-H → O-SiMe2tBu •
Reagents: Chiral catalyst • Fluoride, R4N+ • DDQ • DMSO, Py·SO3 (Parikh-Doering) • PPh3=CH2 • Fluoride, R4N+ • DMSO, Py·SO3 (Parikh-Doering) • NEt3 • Vinyl-Li • BuLi(tert) • MgBr2 • NEt3 • LiN(SiMe3)2 • SiMe3-Cl • HCl • AlH4-Li+ • SiMe2tBu-Cl • DDQ • Grubbs II • AlHiBu2 • Formate, methyl • Dess-Martin • Vinyl-MgX • CeCl3 • SiMe2tBu-Cl • Hydroxide, sodium • PPh3, DEAD • HCl, H2O • Grubbs II • Dess-Martin • Grubbs II •

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