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

• a means to generate appropriate derivatives. This is of course a special case of directed aromatic functionalization. A significant example of this chemistry was key to our synthesis of nothapodytine B, 36 (Figure 1) [63]. This substance is also known as mappicine ketone, in that it is an oxidized

Directed aromatic functionalization

• Victor Snieckus

Beilstein J. Org. Chem. 2011, 7, 1215–1218, doi:10.3762/bjoc.7.141

• . Kingston, August 2011 Victor Snieckus Directed aromatic functionalization methods.