Deoxygenation erythromycin

Analogous deoxygenations were carried out with antibiotics such as nargenicin,[42] fortimicin,[43] seldomycin,[44 erythromycin,[45H47] with baccatin (taxol group),[48] the triquinane hirsuten,[49] the tuberculosis inhibitor a-C-mannobioside,[49a] and the steroids alisol,[50] and progesterone.[51]... 

Miller also explored the ASD of glycerol derivatives through an enantioselective acylation process which relies on the use of a pentapeptide-catalyst which incorporates an A-terminal nucleophilic 3-(l-imidazolyl)-(5)-alanine residue [171], Most recently, Miller has probed in detail the role of dihedral angle restriction within a peptide-based catalyst for ferf-alcohol KR [172], site selective acylation of erythromycin A [173], and site selective catalysis of phenyl thionoformate transfer in polyols to allow regioselective Barton-McCombie deoxygenation [174],... 

Scheme 7. Hypothetical deoxygenation pathways to the two deoxysugar moieties in erythromycin A (14)...

One of the most impressive synthetic achievements with the P-based mediators is the deoxygenation of an erythromycin B derivative towards the industrial synthesis of ABT-229, a potent motilin receptor agonist. Clean... 

We were thus equipped with a new tool to explore selective deoxygenation of erythromycin A beyond the 2 -hydroxyl (Scheme 9). It should be noted that this particular effort in site-selective chemistry was preceded by necessary studies in... 

Scheme 9 Site-selective deoxygenation of Erythromycin A (40) to analogs 70 and 72 via exploitation of innate reactivity of 2 -hydroxyl and the peptide catalyzed phosphitylation of the 4"-hydroxyl, respectively [119]...

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