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Total synthesis of Azaspirene:
Reference: Hayashi, Y.; et al.. J. Am. Chem. Soc. 2002, 124, 12078 (Angiogenesis inhibitor). DOI
Keywords: Alkene -> Diol-1,2 --- Diol -> Ketal --- O-H -> O-SiiPr3 --- CarboxAcid -> CarboxCl --- Ketal -> Diol --- Alkyl-OH -> Ketone-α-OR --- Allyl-OH -> Enone --- O-SiiPr3 -> O-H --- Ketene acetal+Aldehyde --- Aldol-Si --- Mukaiyama Aldol --- Ketone enolate+Aldehyde --- Aldol-Li -> Enone --- Alkyne Hydroamination --- Lactam-5 --- Ketone -> Vinyl-OR --- Sharpless dihydroxylation --- Alkene -> Diol-1,2(asym)
Reagents: OsO4 --- Me2C(OMe)2 --- LiNiPr2 --- MgBr2 --- SiiPr3-OTf --- Hydroxide, lithium --- Oxalyl chloride --- NaH --- CF3CO2H --- Dess-Martin --- LiNiPr2, HMPA --- Dess-Martin --- TsOH --- NH4F --- SiMe2tBu-OTf --- NH3 --- DMF (solvent)

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