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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 • Allyl-OH → Enone • 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, R4N+ • DDQ • DMSO, Py·SO3 (Parikh-Doering) • PPh3=CH2 • Fluoride, R4N+ • DMSO, Py·SO3 (Parikh-Doering) • 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, H2O • Grubbs II • Dess-Martin •

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