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Total synthesis of Calcimycin:
Reference: Boeckman, R. K. Jr.; Charette, A. B.; Asberom, T.; Johnston, B. H. J. Am. Chem. Soc. 1987, 109, 7553; DOI
Keywords: O-MOM -> O-H --- Jones oxidation --- Alkyl-OH -> CarboxAcid --- CarboxAcid -> CarboxEster(thio) --- O-SiMe2tBu -> O-H --- Jones oxidation --- Alkyl-OH -> CarboxAcid --- CarboxEster -> CarboxAcid --- Simmons-Smith --- Li/Sn -> Li-Vinyl --- Li-Vinyl+Alkyl-X --- Cyclopropane opening --- Spiroketal --- Ether-6 --- CarboxAcid -> CarboxEster(thio) --- Friedel-Crafts --- Oxazoline synthesis --- Li-Sulfide+Borane --- Li-Sulfide+Borane --- Li/H -> Li-Vinyl-OR --- Li-Vinyl -> Sn-Vinyl --- Metalate rearrangement (B) --- Dehydration -> Vinyl-OR --- Ether-6 --- B-Allyl-Ipc+Aldehyde --- Sn-Allyl+Aldehyde --- Ozonolysis --- Hydroboration Alkene --- Alkyl-OH -> Alkyl-Br --- O-H -> O-SiMe2tBu
Reagents: BuLi(n) --- CH2I2 --- TsOH --- CrO3, H2SO4 (Jones) --- PPh3 --- Disulfide, pyridyl --- Pyrrolyl-MgX --- Fluoride, Bu4N+ --- CrO3, H2SO4 (Jones) --- BOP --- LiSPr --- Crotyl-SnR3 --- MgBr2 --- BH3·THF --- LiCHR-SPh --- LiCHR-SPh --- HgCl2 --- H2O2 --- MeSO2Cl, NEt3 --- SiMe2tBu-Cl --- O3 --- Me2S --- Crotyl-B(Ipc)2 --- BH3·THF --- H2O2, NaOH --- PPh3, CBr4 --- BuLi, KOtBu --- SnBu3-Cl --- Vinyl-SnR3 --- Imidazole --- HMPA (solvent)

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