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Total synthesis of Erythronolide, (9S)-Dihydro :
Reference: Stürmer, R.; Hoffmann, R. W. Chem.Ber. 1994, 127, 2519. DOI
Keywords: CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • O-H → O-PMB • Ketal → Ketone • Aldehyde → CarboxAcid • Ozonolysis • HWE → EnoateEster • Sharpless epoxidation • B-Allyl+Aldehyde • High pressure • Epoxide reduction • Alkene cleavage • Alkene cleavage • Lactone-9+ • Ketal → Diol-1,3 • B-Allyl+Aldehyde • High pressure •
Reagents: O3 • PPh3 • PPh3=C(Me)-CO2R • AlH4-Li+ • Hydroperoxide, tbutyl • Ti(OiPr)4 • RuO4-Pr4N+ • Alkyl-MgX • AlH4-Li+ • PMB-Cl • OsO4, NMO • Periodate, sodium • DDQ • HCl • OsO4, NMO • Periodate, sodium • CrO3 • HCl, H2O • Benzoyl chloride, 2,4,6-trichloro • DMAP •

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