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Total synthesis of Maoecrystal Z:
Reference: Cha, J. Y.; Yeoman, J, T. S.; Reisman, S. E. J. Am. Chem. Soc. 2011, 133, 14964–14967.. DOI
Keywords: O-SiMe2tBu → O-H • O-H → O-C(O)R • Ozonolysis • O-C(O)R → O-H • Alkyl-OH → Aldehyde • CarboxAmide enolate(Myers)+Alkyl-X • Alkyl-X+Enolate • CarboxAcid → CarboxAmide • CarboxAmide → Alkyl-OH • Lactone enolate+Alkyl-X • Alkyl-X+Enolate • Lactone → EneLactone • Selenoxide-Ei → EneLactam • Radical cyclization(Ketyl) • Aldehyde → Enal • O-H → O-SiMe2tBu • Epoxidation, peracid • Epoxide reductive alkylation •
Reagents: Chiral auxiliary-Myers • Piv-Cl • Pseudoephedrine • LiNiPr2 • BH3·NH3 • LiNiPr2 • PPh3, I2 • LiN(SiMe3)2 • HMPA (solvent) • KN(SiMe3)2 • SePh-Br • H2O2 • H2SiF6 • SmI2 • Acetic anhydride • O3 • CH2=NMe2+I- • Hydroxide, sodium • Dess-Martin • Perbenzoic acid, 3-chloro •

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