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.
Zakarian
Joseph E
JE
Department of Chemistry, Université de Montréal, Montréal, Québec, Canada.
El-Azizi
Yassir
Y
Collins
Shawn K
SK
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