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Total synthesis of Sundiversifolide:
Reference: Ohtsuki, K.; Matsuo, K.; Yoshikawa, T.; Moriya, C.; Tomita-Yokotani, K.; Shishido, K.; Shindo, M. Org. Lett. 2008, 10, 1247-1250. DOI
Keywords: Mg-Vinyl+Ketone • O-H → O-SiPh2tBu • O-H → O-SiMe2tBu • O-SiPh2tBu → O-H • Finkelstein reaction • Li/I → Li-Alkyl • Li-Alkyl+CarboxEster • CarboxEster+Li-R • CompE+-Alkyl-I/Ketone+Li-R • O-H → O-SiPh2tBu • O-SiMe2tBu → O-H • Alkyl-OH → Ketone • O-SiPh2tBu → O-H • Epoxidation, peracid • Dehydration → Ene • Li-Alkynyl+Aldehyde • Li/H → Li-Alkynyl • Hydroalumination Alkyne • CarboxAmide enolate(Evans)+Alkyl-X • Alkyl-X+Enolate • Sharpless dihydroxylation • Alkene → Diol-1,2(asym) • Wittig-carboxymethyl → EnoateEster • Lactone-5 • Hydrogenation EnoateEster • Epoxide reduction •
Reagents: BuLi(n) • Formaldehyde • AlH2(OR)2-Na+ • AlH2(OR)2-Na+ • Sulfonyl chloride, methane, NEt3 • BuLi(tert) • Vinyl-MgX • SiPh2tBu-Cl • Chiral auxiliary-Evans • LiNiPr2 • Sulfonamide, methane • SiMe2tBu-Cl • Fluoride, R4N+ • Sulfonyl chloride, methane, NEt3 • Iodide, sodium • SiPh2tBu-Cl • HCl, H2O • RuO4-Pr4N+, NMO • PPh3=C(Me)-CO2R • Fluoride, R4N+ • Perbenzoic acid, 3-chloro • NiCl2 • SOCl2 • ZnI2 • BH3CN-Na+ • BH4-Na+ • Iodide, sodium •

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