Improved procedure for the enantiometric synthesis of 1-hydroxy/acetoxy-2,6-diaryl-3,7-dioxabicycl.
Short enantiomeric syntheses of the 1-hydroxy/acetoxy-3,7-dioxabicyclo[3.3.0]octane lignans, paulownin, and (+)-phrymarin I and II, were accomplished by starting from the chiral synthon, (R)-(+)-3-hydroxybutanolide, and employing photocyclization as the key step.
Ishibashi
F
F
Faculty of Fisheries, Nagasaki University, Japan. fumito@net.nagasaki-u.ac.jp
Hayashita
M
M
Okazaki
M
M
Shuto
Y
Y
D001952:Bridged-Ring Compounds / Q000138:chemical synthesis / Q000737:chemistry; D000440:Butanols / Q000737:chemistry*; D003500:Cyclization; D004149:Dioxoles / Q000138:chemical synthesis* / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D008027:Light; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D001952:Bridged-Ring Compounds; D000440:Butanols; D004149:Dioxoles; D005663:Furans; D017705:Lignans; C432584:phrymarin I; C432585:phrymarin II; C008773:paulownin