Total synthesis of Illudin M:
| Reference: | Kinder, F. R.; Bair, K. W. J. Org. Chem. 1994, 59, 6965 DOI |
| Reactions: | Ketone+Mg-Alkyl • Mg-Alkyl+Ketone • CompE+-Ketone/Ketone+M-R • Allylic oxidation → Enone • Carbonyl oxide Cycloaddition • Bicyclo(221)-oxa • Ether-5 • Spiro(52) • Diazoketone • Jones oxidation • Allyl-OH → Enone • Dehydroalkoxylation → Enone • Dehydroalkoxylation → Enone • Enone → Allyl-OH • |
| Reagents: | Me-MgCl • Hydroxide, potassium • CrO3, H2SO4 (Jones) • AlH4-Li+ • NBS • Diazoketone • Rh2(OAc)4 • HOMe (react) • |