Total Synthesis of Angucyclines, 1. - Synthesis of a Daunomycinone-Rabelomycin Hybrid

The synthesis of the racemic angucyclinone hybrid 3 which combines the structural features of rabelomycin (1) and daunomycinone (2) is described. Key steps are the cyclization of the bromide 6b by a Marshalk‐type reaction to yield the angular skeleton 7b, introduction of the tertiary hydroxy group b...

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Veröffentlicht in:Liebigs Annalen der Chemie 1993-08, Vol.1993 (8), p.911-913
Hauptverfasser: Krohn, Karsten, Ballwanz, Frank, Baltus, Wolfgang
Format: Artikel
Sprache:eng
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Zusammenfassung:The synthesis of the racemic angucyclinone hybrid 3 which combines the structural features of rabelomycin (1) and daunomycinone (2) is described. Key steps are the cyclization of the bromide 6b by a Marshalk‐type reaction to yield the angular skeleton 7b, introduction of the tertiary hydroxy group by bromination to 11, solvolysis to 12 and photoinduced oxygenation to afford the C‐1 ketone 3.
ISSN:0170-2041
1099-0690
DOI:10.1002/jlac.1993199301143