A short enantioselective total synthesis of the fundamental pentacyclic triterpene lupeol.
The first enantioselective synthesis of lupeol has been developed by applying two carefully crafted cation-pi cyclization stages to generate the pentacyclic structure with complete stereocontrol. The synthesis (Scheme 1) is noteworthy because of its brevity and also because it solves a longstanding problem in the field of natural product synthesis.
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Karavadhi
K
Surendra
E J
EJ
Corey
D003500:Cyclization; D015394:Molecular Structure; D053978:Pentacyclic Triterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism; D000094042:Lupanes
D053978:Pentacyclic Triterpenes; C010480:lupeol; D000094042:Lupanes