Synthesis of louisianin C.
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.
Beierle
John M
JM
Department of Chemistry, Eugene F. Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467, USA.
Osimboni
Ekundayo B
EB
Metallinos
Costa
C
Zhao
Yajun
Y
Kelly
T Ross
TR
D000470:Alkaloids / Q000032:analysis / Q000138:chemical synthesis*; D000498:Allyl Compounds / Q000032:analysis / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D005459:Fluorides / Q000737:chemistry; D015394:Molecular Structure; D011725:Pyridines / Q000032:analysis / Q000138:chemical synthesis*; D012821:Silanes / Q000737:chemistry; D013302:Streptomyces / Q000737:chemistry
D000470:Alkaloids; D000498:Allyl Compounds; D011725:Pyridines; D012821:Silanes; C096932:louisianin C; D005459:Fluorides