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Total synthesis of Aspicillin:
Reference: Oppolzer, W.; Radinov, R. N.; DeBrabander, J. Tetrahedron Lett. 1995, 36, 2607. DOI
Keywords: O-THP → O-H • Selenide → Selenoxide • O-SiMe2tBu → O-H • Acetoxonium • Mg-Alkyl+Epoxide • Epoxide+Mg-R • CarboxEster → Ketene acetal • Selenoxide-Ei → EnoateEster • CarboxEster → EnoateEster • Epoxidation, V • Epoxide → Diol • Hydroboration Alkyne • CompRed-Alkene/Aldehyde+M-H • B-R → Zn-R • Zn-Vinyl+Aldehyde • Aldehyde+Zn-R • Lactone-9+ • CompE+-Aldehyde/CarboxEster+M-R • CarboxAcid → CarboxEster • Alkyl-OH → Aldehyde • O-H → O-C(O)R • O-H → O-SiMe2tBu • CarboxEster → CarboxAcid •
Reagents: Epoxide • Alkyl-MgX • Cu(COD)Cl • Carbodiimide • TsOH • DMSO, (COCl)2 (Swern) • Chiral catalyst • DBU • LiNiPrCy • SiMe2tBu-Cl • SePh-Br • Perphthalic acid • HF • Hydroperoxide, tbutyl - V • Acetic anhydride • BF3·OEt2 • Bicarbonate, sodium • HCl, MeOH • Vinyl-ZnX •

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