Total synthesis of (+/-)-syn-copalol.
The labdane diterpene derivative, syn-copalol [(+)-5] is the alcohol part of syn-copalyl diphosphate [(+)-4]. In this paper, racemic (+/-)-5 was synthesized from a known racemic lactone in 8 steps. The current and our previous syntheses provide all four copalol derivatives [(+)-3, (-)-3 and (+/-)-5] which are required for the biosynthetic study of polycyclic diterpenes.
Toshima
Hiroaki
H
Department of Bioresource Science, College of Agriculture, Ibaraki University, Ami-machi, Inashiki-gun, Ibaraki 300-0393, Japan. toshima@ipc.ibaraki.ac.jp
Oikawa
Hideaki
H
Yada
Hiroshi
H
Ono
Hiroshi
H
Toyomasu
Tomonobu
T
Sassa
Takeshi
T
D002384:Catalysis; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D007783:Lactones / Q000737:chemistry; D010755:Organophosphates / Q000737:chemistry*; D013237:Stereoisomerism
D004224:Diterpenes; D007783:Lactones; D010755:Organophosphates; C408747:copalyl diphosphate; C433017:labdane; C475224:copalol