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Total synthesis of Imperanene:
Reference: Shattuk, J. C.; Shreve, C. M.; Solomon, S. E. Org. Lett. 2001, 3, 3021. DOI
Keywords: O-H → O-SiMe2tBu • Alkyl-OH → Aldehyde • O-Bn → O-H • O-SiMe2tBu → O-H • Ozonolysis C=N • Wittig-benzyl → Styrene • Hydroboration alkene • SAMP hydrazone • Aldehyde azaenolate(asym)+Alkyl-X • Alkyl-X+Azaenolate •
Reagents: SiMe2tBu-Cl • BH(Siam)2 • CrO3Cl·PyH (PCC) • O3 • PPh3=CH-Ar • SPh-SiMe3 • Fluoride, R4N+ • Imidazole • LiNiPr2 • Chloromethyl ether • Chiral auxiliary-SAMP •

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