Tandem Conjugate Cyanide Addition−Dieckmann Condensation in the Synthesis of the ABCD-Ring System of Lactonamycin

Tandem Conjugate Cyanide Addition−Dieckmann Condensation in the Synthesis of the ABCD-Ring System of Lactonamycin

An efficient synthesis of the ABCD-ring system of lactonamycin (1) is reported in this Letter. The key step is the tandem cyanide conjugate addition−Dieckmann condensation of alkyne 17 to afford a fully functionalized anthracene. Selective reduction of the cyano group with subsequent lactam formatio...

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Veröffentlicht in:Organic letters 2002-04, Vol.4 (8), p.1403-1405
Hauptverfasser: Deville, Jay P, Behar, Victor
Format: Artikel
Sprache:eng
Schlagworte:
Anti-Bacterial Agents - chemical synthesis
Cyanides - chemistry
Indicators and Reagents
Indoles - chemical synthesis
Models, Biological
Naphthoquinones - chemical synthesis
Streptomyces - chemistry
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Zusammenfassung:An efficient synthesis of the ABCD-ring system of lactonamycin (1) is reported in this Letter. The key step is the tandem cyanide conjugate addition−Dieckmann condensation of alkyne 17 to afford a fully functionalized anthracene. Selective reduction of the cyano group with subsequent lactam formation affords the tetracyclic core of lactonamycin 19.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0257373