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

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