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Total synthesis of Zearolone:
Reference: Kalivretenos, A.; Stille, J, K,; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883. DOI
Keywords: Li-Aryl → I-Aryl • CarboxAmide → CarboxEster • O-H → O-MEM • O-H → O-SiMe2tBu • Alkyl-OH → Alkyl-Br • Mitsunobu → Br • Corey-Kim • Alkyl-OH → Aldehyde • O-SiMe2tBu → O-H • Mitsunobu → Ester • Alkyl-OH → Alkyl-OC(O)R • Cu-Vinyl+Epoxide • Epoxide+Cu-R • Hydroboration alkene • Mg-Alkyl+Aldehyde • Aldehyde+Mg-R • Li/H → Li-Aryl • O-MOM → O-H • Pd/Sn-Vinyl+Aryl-X • Stille coupling • Lactone-9+ •
Reagents: BuLi(tert) • ICl • Me3O+ X- • Carbonate, sodium • MEM-Cl • Hydroxide, lithium • Vinyl-MgX • CuI • SiMe2tBu-Cl • BH-BBN • CBr4 • Mg° • NCS • Fluoride, R4N+ • DEAD • Pd(PPh3)4 • HCl, H2O •

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