Total synthesis of Pupukeanone:
| Reference: | Schiehser, G. H.; White, J. D. J. Org. Chem. 1980, 45, 1864. DOI |
| Reactions: | Birch reduction • Simmons-Smith • Cyclopropane • Bicyclo(410) • Fischer esterification • Enone → Ketal(Me) • Diazoester Cyclopropanation • Cyclopropane • Mg-Vinyl+Ketone • Mg-Vinyl+Aldehyde • Ketal → Vinyl-OR • Hydrogenation Diene • Cyclopropane alkylation • Diels-Alder, Intram, Ene • Bicyclo(222) • CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • Allyl-OH → Enone • Dehydration → Diene • Enone → Ketal(Me) • |
| Reagents: | CH2I2, Zn/Ag • Diazoacetate • HCl • Orthoformate • AlH4-Li+ • DMSO, Py·SO3 (Parikh-Doering) • DMSO, Py·SO3 (Parikh-Doering) • Vinyl-MgX • Propenyl-MgX • DMSO (solvent) • H2, Pt • Butadiene, 2-OR • |