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

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