First total synthesis of (R,R,R)- and (3R,5S,9R)-bejarol by gold-catalyzed allene cycloisomerization and determination of absolute configuration of the natural product.
The first total synthesis of (R,R,R)-bejarol and its (3R,5S,9R)-isomer has been accomplished which confirms the absolute configuration of the natural products. The key step is the gold-catalyzed cycloisomerization of the enantiomerically pure beta-hydroxyallenes 12/13 to the corresponding dihydropyrans 14/15.
Sawama
Yoshinari
Y
Organic Chemistry II, Dortmund University of Technology, D-44227, Dortmund, Germany.
Sawama
Yuka
Y
Krause
Norbert
N
D000466:Alkadienes / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D007536:Isomerism; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry
D000466:Alkadienes; D001688:Biological Products; D012717:Sesquiterpenes; C534476:bejarol; C025947:propadiene; D006046:Gold