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