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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 • Acetic acid, trifluoro • Dess-Martin • LiNiPr2, HMPA • Dess-Martin • TsOH • Fluoride, ammonium • SiMe2tBu-OTf • NH3 • DMF (solvent) •

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