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Total synthesis of Callystatin A:
Reference: Marshall, J. A.; Bourbeau, M. P. J. Org. Chem. 2002, 67, 2751
Keywords: O-H -> O-SiMe2tBu --- O-PMB -> O-H --- Alkyl-OH -> Aldehyde-α-OR --- Allyl-OH -> Allyl-Br --- Allyl-Br -> Allyl-Phosphonium --- EnoateEster -> Allyl-OH --- Alkyl-OH -> Alkyl-I --- O-Bn -> O-H --- Alkyl-OH -> Aldehyde --- Ozonolysis --- EnoateEster -> Allyl-OH --- Allyl-OH -> Enal --- O-H -> O-SiMe3 --- O-SiMe3 -> O-H --- Alkyl-OH -> Ketone --- O-SiMe2tBu -> O-H --- Allyl-OH -> EneLactone --- Lactone-6 --- Sn-Allenyl+Aldehyde --- Zn-Allenyl+Aldehyde --- Li-Alkynyl+Epoxide --- Pd/B-Alkyl+Vinyl-X --- Suzuki coupling --- Wittig-carboxymethyl -> EnoateEster --- Hydrostannation Alkyne --- Seyferth-Gilbert homologation --- Aldehyde -> Alkyne --- Hydrogenation-Lindlar --- HWE -> EnoateEster-cis --- Wittig-allyl -> Diene --- Li/I -> Li-Alkyl --- Li-Alkyl+Borane --- Hydrogenation-Alkyne --- Hydrogenation-Lindlar --- Sn-Vinyl -> Vinyl-I
Reagents: Epoxide --- Alkynyl-Li --- BF3·OEt2 --- SiMe2tBu-Cl --- H2, Pd --- DDQ --- DMSO, (COCl)2 --- P(O)(OCH2CF3)2CHMe-CO2Me --- PPh3, CBr4 --- PBu3 --- AlHiBu2 --- KOtBu --- TsOH·Py --- PPh3, I2 --- Alkyl-Li --- Allenyl-SnR3 --- BF3·OEt2 --- SiMe2tBu-OTf --- H2, Pd --- DMSO, (COCl)2 --- Allenyl-ZnX --- H2, Pd --- O3 --- Ph3P=C(Me)-CO2R --- AlHiBu2 --- MnO2 --- Diazophosphonate --- SiMe3-Cl --- TsOH·Py --- HSnBu3 --- I2 --- BuLi(tert) --- 9-BBN-OMe --- PdCl2(dppf) --- Dess-Martin --- HF·NEt3 --- MnO2 --- PdCl2(PPh3)2 --- Vinyl-SnR3 --- Imidazole --- Imidazole

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