Total synthesis of (+)-cyperolone.
The total synthesis of (+)-cyperolone, an eudesmane-derived sesquiterpenoid from Cyperus rotundus, is described. The de novo synthesis was accomplished via a 15 step sequence starting from (R)-(-)-carvone. The synthetic route features a platinum-catalyzed cycloisomerization to rapidly construct the bicyclic core from a 3-silyloxy-1,5-enyne intermediate.
Organic Chemistry, Bergische Universität Wuppertal, Gaussstr. 20, 42119 Wuppertal, Germany.
Philipp
P
Klahn
Alexander
A
Duschek
Clémence
C
Liébert
Stefan F
SF
Kirsch
D002384:Catalysis; D003500:Cyclization; D000081005:Cyclohexane Monoterpenes; D029786:Cyperus / Q000737:chemistry; D007536:Isomerism; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry; D010984:Platinum / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013729:Terpenes / Q000138:chemical synthesis*
D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes; D012717:Sesquiterpenes; D013729:Terpenes; C572274:cyperolone; D010984:Platinum; C006923:carvone