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Total synthesis of Callystatin A:
Reference: Marshall, J. A.; Bourbeau, M. P. J. Org. Chem. 2002, 67, 2751. DOI
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 -> B-Alkyl • Borane+Li-Alkyl • 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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