Synthesis of decalin type chiral synthons based on enzymatic function.
Enzymatic monobenzoylation of (+/-)-2-hydroxy-decahydro-5,5,8a-trimethyl-1-naphthalenemethano l derivatives (1-4) using vinyl benzoate in organic solvent gave the optically active diols (1-4) and monobenzoates (16-19). The enantiomeric excess (ee) of the enzymatic reaction products were found to be in the range of 11% to 49%. On the other hand, enzymatic hydrolysis of the acetoxybenzylidene acetal (+/-)-25d, e was found to give more than 90% ee of (10aS)-25d, e in moderate yield. Finally, the 90% ee of (10aS)-25e was converted to the 90% ee of the desired (8aS)-1.
Nozawa
M
M
School of Pharmaceutical Sciences, Toho University, Funabashi, Chiba, Japan.
Murakami
Y
Y
Noda
K
K
Tamatsukuri
R
R
Kato
K
K
Akita
H
H
D004798:Enzymes / Q000737:chemistry*; D006868:Hydrolysis; D009281:Naphthalenes / Q000737:chemistry*; D013057:Spectrum Analysis; D013237:Stereoisomerism
D004798:Enzymes; D009281:Naphthalenes; C007229:decalin