Formal Synthesis of 6-Deoxyerythronolide B

Formal Synthesis of 6-Deoxyerythronolide B

The enantioselective synthesis of the carbon skeleton of 6-deoxyerythronolide B has been achieved in 23 linear steps from propionaldehyde. The synthesis relies on an iterative approach employing an asymmetric acyl-thiazolidinethione propionate aldol reaction to establish eight of nine stereogenic ce...

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Veröffentlicht in:Organic letters 2006-05, Vol.8 (10), p.2191-2194
Hauptverfasser: Crimmins, Michael T, Slade, David J
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Erythromycin - analogs & derivatives
Erythromycin - chemical synthesis
Erythromycin - chemistry
Molecular Structure
Thiazolidines - chemistry
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Zusammenfassung:The enantioselective synthesis of the carbon skeleton of 6-deoxyerythronolide B has been achieved in 23 linear steps from propionaldehyde. The synthesis relies on an iterative approach employing an asymmetric acyl-thiazolidinethione propionate aldol reaction to establish eight of nine stereogenic centers. The remaining stereogenic center at C6 was set through a Myers alkylation employing a complex alkyl iodide.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0607241