Total synthesis of (S)-(+)-curcudiol, and (S)-(+)- and (R)-(-)-curcuphenol.
A highly enantioselective synthesis of the versatile chiral synthons possessing one stereogenic center, (S)- and (R)-4-aryl-5-hydroxy-(2E)-pentenoate (3) was achieved based on the enzymatic reaction of (+/-)-3 with commercially available lipases MY-30 or OF-360 from Candida rugosa. Application of (S)-3 and (R)-3 to the total syntheses of(S)-curcuphenol (1), (S)-curcudiol (2), and (R)-curcuphenol (1), respectively, is described.
Ono
M
M
School of Pharmaceutical Sciences, Toho University, Funabashi, Chiba, Japan.
Ogura
Y
Y
Hatogai
K
K
Akita
H
H
D002851:Chromatography, High Pressure Liquid; D004800:Enzymes, Immobilized; D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D008049:Lipase / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004800:Enzymes, Immobilized; D005233:Fatty Alcohols; D007202:Indicators and Reagents; D010636:Phenols; D012717:Sesquiterpenes; C454669:curcudiol; C054389:curcuphenol; D008049:Lipase