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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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