Total synthesis of Virosaine A:
| Reference: | Hughes, J. M. E.; Gleason, J. L. Tetrahedron 2018, 74, 759-768. DOI |
| Reactions: | Diels-Alder, Enal (asym) • Furan cycloaddition • Bicyclo(221)-oxa • Ether-5 • Li-Alkyl+Aldehyde • Acetal → Aldehyde • Aldehyde → Oxime • Bromohydrin → Epoxide • Epoxidation via halohydrin • Oxime → Nitrone • Nitrone synthesis • Nitrone Cycloaddition • Bicyclo(321)-aza • Bicyclo(530)-aza • O-H → O-C(O)NR2 • Li/H → Li-Ether • Li-Alkyl → Br-Alkyl • Radical alkylation (Keck) Sn-Allyl • O-C(O)NR2 → O-H • Ozonolysis • Lactol → Lactone • Lactone-5 • Dehydroalkoxylation → EnoateEster • |
| Reagents: | Acrolein • Chiral catalyst (amino-alcohol) • Alkyl-Li • HCl • NH2OH • NaH • Acetic acid • O=C(Imid)2 • BuLi(sec) • Br2 • Allyl-SnR3 • AIBN • AlH4-Li+ • O3; Me2S • Dess-Martin • Pyridine • Al2O3 • |