Total Synthesis of Everninomicin 13,384-1-Part 3: Synthesis of the DE Fragment and Completion of the Total Synthesis

The stereoselective construction of the DE fragment (2) of everninomicin 13,384‐1 (1) is reported. From the two possible ways of inserting the DE fragment between the A1B(A)C and FGHA2 domains of the natural product, the sequence involving the DEFGHA2 segment was found to be the most viable. This co...

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Veröffentlicht in:	Chemistry : a European journal 2000-09, Vol.6 (17), p.3149-3165
Hauptverfasser:	Nicolaou, K. C., Mitchell, Helen J., Rodríguez, Rosa Maria, Fylaktakidou, Konstantina C., Suzuki, Hideo, Conley, Scott R.
Format:	Artikel
Sprache:	eng
Schlagworte:	Aminoglycosides Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry carbohydrates everninomicin Molecular Structure orthoester formation phenylseleno glycoside Spectrum Analysis stereocontrolled glycosidation
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description	The stereoselective construction of the DE fragment (2) of everninomicin 13,384‐1 (1) is reported. From the two possible ways of inserting the DE fragment between the A1B(A)C and FGHA2 domains of the natural product, the sequence involving the DEFGHA2 segment was found to be the most viable. This coupling was followed by attachment of a suitably protected and activated A1B(A)C fragment which led, after orthoester construction and final deprotection to the targeted everninomicin 13,384‐1 (1), completing the total synthesis of this complex naturally occurring substance.
doi_str_mv	10.1002/1521-3765(20000901)6:17<3149::AID-CHEM3149>3.0.CO;2-L
format	Article
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subjects	Aminoglycosides Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry carbohydrates everninomicin Molecular Structure orthoester formation phenylseleno glycoside Spectrum Analysis stereocontrolled glycosidation
title	Total Synthesis of Everninomicin 13,384-1-Part 3: Synthesis of the DE Fragment and Completion of the Total Synthesis
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