image

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 • O-SiMe2tBu → O-H • Jones oxidation • Simmons-Smith • Cyclopropane • Cyclopropane alkylation • Spiroketal • Ether-6 • Alkyl-OH → CarboxAcid • Pyrrole synthesis • Mg-Aryl+CarboxEster • Oxazole synthesis • Li-Sulfide+Borane • Li-R → Sn-R • Metalate rearrangement (B) • B-Alkyl → HO-Alkyl • Dehydration → EnolEther • Ether-6 • Sn-Allyl+Aldehyde • Aldehyde+Sn-R • Felkin-Anh Chelation • Ozonolysis • Hydroboration alkene • Alkyl-OH → Alkyl-Br • Appel → Br • O-H → O-SiMe2tBu • Li/Sn → Li-Vinyl • Li-Vinyl+Alkyl-X • Alkyl-X+Li-R • B-Allyl-Ipc+Aldehyde • CarboxEster → CarboxAcid • N-C(O)R → N-H • Alkyl-OH → CarboxAcid • CarboxAcid → CarboxEster(thio) • Li/H → Li-Vinyl-OR •
Reagents: CH2I2, ZnEt2 • TsOH • CrO3, H2SO4 (Jones) • PPh3 • Disulfide, pyridyl • Pyrrolyl-MgX • Fluoride, R4N+ • CrO3, H2SO4 (Jones) • BOP • Thiolate, propyl • Crotyl-SnR3 • MgBr2 • BH3·THF • LiCHR-SPh • HgCl2 • H2O2 • Sulfonyl chloride, methane, NEt3 • SiMe2tBu-Cl • O3 • Me2S • BH3·THF • H2O2, NaOH • PPh3, CBr4 • BuLi, KOtBu • SnBu3-Cl • Imidazole • HMPA (solvent) • BuLi(n), HMPA • Vinyl-SnR3 • Crotyl-B(Ipc)2 • Chiral auxiliary-Boronate • SiMe2tBu-Cl • HMPA (solvent) • Vinyl-SnR3

Syntheses Home