Exploiting quadrupolar interactions in the synthesis of the macrocyclic portion of longithorone C.
2,3,4,5,6-Pentafluorobenzyl and 3,5-bistrifluoromethylbenzyl ester auxiliaries can enable difficult macrocyclizations to afford rigid all-carbon paracyclophanes. The effectiveness of these auxiliaries has been demonstrated in preparing the carbon skeleton of the macrocyclic natural product longithorone C.
Department of Chemistry, Université de Montréal, Montréal, Québec, Canada.
Joseph E
JE
Zakarian
Yassir
Y
El-Azizi
Shawn K
SK
Collins
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure
D001688:Biological Products; D001952:Bridged-Ring Compounds; D006845:Hydrocarbons, Fluorinated; C530915:longithorone C