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Total synthesis of Calarene:
Reference: Coates, R. M.; Shaw, J. E. J. J. Am. Chem. Soc. 1970, 92, 5657 DOI
Keywords: Dehydration → Enone • Ketone → Enamine • Robinson annulation, enamine • Enamine ConjAdd • Enone → Ketal(thio) • Ketal(thio) → CH2 • Ketone → CH2 • Claisen acylation, carbonate • Ketone enolate+Carbonate • CompE+-CarboxEster/Ketone+Li-Alkyl • Li-Me+Ketoester • Pyrazoline synthesis • Cyclopropane • Azo fragmentation •
Reagents: Pyrrolidine • Methyl vinyl ketone • Acetate, sodium • Acetic acid • TsOH • H2, RaNi • NaH • O=C(OR)2 • MeLi • HCl • Hydrazine • Hydroxide, potassium •

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