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 formation affords the tetracyclic core of lactonamycin 19. [reaction: see text]
Deville
Jay P
JP
Department of Chemistry MS-60, Rice University, Houston, Texas 77251-1892, USA.
Behar
Victor
V
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D003486:Cyanides / Q000737:chemistry; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis*; D008954:Models, Biological; D009285:Naphthoquinones / Q000138:chemical synthesis*; D013302:Streptomyces / Q000737:chemistry
D000900:Anti-Bacterial Agents; D003486:Cyanides; D007202:Indicators and Reagents; D007211:Indoles; D009285:Naphthoquinones; C102442:lactonamycin