Beierle John M, Osimboni Ekundayo B, Metallinos Costa, Zhao Yajun, Kelly T Ross
Department of Chemistry, Eugene F. Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467, USA.
J Org Chem. 2003 Jun 13;68(12):4970-2. doi: 10.1021/jo0341618.
The synthesis of louisianin C (3), a member of a small family of 3,4,5-trisubstituted pyridyl natural products, is achieved in six steps and 11% overall yield starting from commercially available 3,5-dibromopyridine. The key step is a fluoride-induced desilylation-cyclization to afford carbinol 12.