Directed aromatic functionalization in natural-product synthesis: Fredericamycin A, nothapodytine B, and topopyrones B and D

• Charles Dylan Turner and
• Marco A. Ciufolini

Beilstein J. Org. Chem. 2011, 7, 1475–1485, doi:10.3762/bjoc.7.171

• activity: Fredericamycin A, nothapodytine B, and topopyrones B and D. In each case, directed aromatic functionalization methodology greatly facilitated the assembly of the key molecular subunits. Keywords: alkaloids; directed aromatic functionalization; fredericamycin; heterocyclic compounds; lithiation

• ; nothapodytine; organolithium compounds; topopyrone; Review Our laboratory is primarily interested in the total synthesis of natural products, and does not conduct research on directed aromatic functionalization ("DAF") per se. On numerous occasions, however, DAF technology has been key to the success of

• specific synthetic endeavors in our group. Herein, we illustrate the application of such techniques to three representative problems that we have addressed over the years: The syntheses of fredericamycin A, nothapodytine B, and topopyrones B and D. Fredericamycin A This initial portion of the present