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Total synthesis of Rifamycin S (partial) New:
Reference: Roush, W. R.; Palkowitz, A. D. J. Am. Chem. Soc., 1987, 109, 953. DOI
Keywords: O-H -> OSiEt3 • O-SiEt3 -> O-H • Diol -> Ketal • Ozonolysis • Diol -> Ketal • Alkyl-OH -> Aldehyde • O-H -> O-C(O)R • Ozonolysis • Aldehyde -> Alkyl-OH • O-H -> O-SEM • Ozonolysis • O-C(O)R -> O-H • O-H -> O-Me • Acetal -> Aldehyde • B-Allyl-Tartrate+Aldehyde • Aldol-B-Tartrate • B-Allyl-Tartrate+Aldehyde • Aldol-B-Tartrate • B-Allyl-Tartrate+Aldehyde • Aldol-B-Tartrate • B-Allyl-Tartrate+Aldehyde • Aldol-B-Tartrate • Ozonolysis •
Reagents: Crotyl-B(tartrate) • SiEt3-Cl • Me2S • Crotyl-B(tartrate) • Allyl-B(tartrate) • Propenyl-OR} • O3 • TsOH·Py • Orthoformate • Fluoride, Bu4N+ • DMSO, (COCl)2 • Crotyl-B(tartrate) • Acetic anhydride, Py • O3 • BH4-Na+ • NEtiPr2 • O3 • AlH4-Li+ • KOtBu • MeI • TsOH·Py •

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