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Total synthesis of Rifamycin S (partial):
Reference: Roush, W. R.; Palkowitz, A. D. J. Am. Chem. Soc., 1987, 109, 953. DOI
Keywords: O-H → O-SiEt3 • O-SiEt3 → O-H • B-Allyl-Tartrate+Aldehyde • Aldol-B-Tartrate • B-Allyl-Tartrate+Aldehyde • B-Allyl-Tartrate+Aldehyde • Aldol-B-Tartrate • B-Allyl-Tartrate+Aldehyde • Ozonolysis • Diol-1,3 → Ketal • Ozonolysis • Aldehyde → Acetal(Me) • Alkyl-OH → Aldehyde • O-H → O-C(O)R • Ozonolysis • O-C(O)R → O-H • Ozonolysis • O-H → O-Me • Acetal → Aldehyde • CompNu-Acetal/Ketal+H+ • Aldehyde → Alkyl-OH • O-H → O-SEM •
Reagents: Crotyl-B(tartrate) • Chiral auxiliary-Boronate • SiEt3-Cl • O3 • Crotyl-B(tartrate) • Allyl-B(tartrate) • HCl, H2O • Propenyl-OR • O3 • TsOH·Py • Orthoformate • Fluoride, R4N+ • DMSO, (COCl)2 (Swern) • Crotyl-B(tartrate) • Acetic anhydride, Py • O3 • BH4-Na+ • NEtiPr2 • O3 • AlH4-Li+ • KOtBu • MeI • TsOH·Py •

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