TY - JOUR
T1 - Syntheses of Highly Oxygen-functionalized Derivatives of Dihydrodihydroxyphthalic Acid in Enantiomerically Enriched Forms
AU - Ikeda, Hajime
AU - Hosomi, Hiroyuki
AU - Ohba, Shigeru
AU - Ohta, Hiromichi
AU - Sugai, Takeshi
PY - 1998
Y1 - 1998
N2 - Starting from dihydrodihydroxyphthalic acid (DDP), (1R, 2S, 5R, 6S))-(-)-3,4-bis(benzyloxymethyl)-5-hydroxy-8,8-dimethyl-6,8-dioxabicyelo[4.3.0]non-3-en-2-yl chloroacetate (>95%e.e.), a highly oxygen-functionalized derivative, was prepared by a combination of chemical and enzymatic reactions. The key step for asymmetrization was hydrolysis of the corresponding meso bis-chloroacetate with pig pancreatic lipase.
AB - Starting from dihydrodihydroxyphthalic acid (DDP), (1R, 2S, 5R, 6S))-(-)-3,4-bis(benzyloxymethyl)-5-hydroxy-8,8-dimethyl-6,8-dioxabicyelo[4.3.0]non-3-en-2-yl chloroacetate (>95%e.e.), a highly oxygen-functionalized derivative, was prepared by a combination of chemical and enzymatic reactions. The key step for asymmetrization was hydrolysis of the corresponding meso bis-chloroacetate with pig pancreatic lipase.
KW - dihydrodihydroxyphthalic acid
KW - hydrolysis
KW - meso substrate
KW - photooxygenation
KW - pig pancreatic lipase
UR - http://www.scopus.com/inward/record.url?scp=0342645884&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0342645884&partnerID=8YFLogxK
U2 - 10.1271/bbb.62.396
DO - 10.1271/bbb.62.396
M3 - Article
AN - SCOPUS:0342645884
SN - 0916-8451
VL - 62
SP - 396
EP - 400
JO - Bioscience, Biotechnology and Biochemistry
JF - Bioscience, Biotechnology and Biochemistry
IS - 2
ER -