TY - JOUR
T1 - Syntheses of (+)-exo-, (+)-endo-Brevicomin, and (-)-Frontalin via Enzymatic Reactions
AU - Ishiyama, Jun Ichi
AU - Toi, Manabu
AU - Ichikawa, Chiaki
AU - Oi, Shuichi
AU - Inoue, Yoshio
PY - 1993
Y1 - 1993
N2 - (+)-exo-Brevicomin of enantiomerically pure form and its (+)-endo-isomev of 77% e. e. were synthesized via lipase-eatalyzed acetylation of syn-2-(l-hydroxypropyl)-6-methyl-3,4-dihydro-2 H-pyran (syn-2) and anti-2, respectively, both of which were accessible by stereoselective reduction of 2-propionyl-6-methyl-3, 4-dihydro-2 H-pyran (1). Similarly, (-)-forntalin of 91% e. e. was obtained via consecutive enzymatic hydrolysis or acetylation of 2-methoxycarbonyl (5), 2-hydroxymethyl (6), and 2-acetoxymethyl derivative (7) of 2, 6-dimethyl-3, 4-dihydro-2 H-pyran.
AB - (+)-exo-Brevicomin of enantiomerically pure form and its (+)-endo-isomev of 77% e. e. were synthesized via lipase-eatalyzed acetylation of syn-2-(l-hydroxypropyl)-6-methyl-3,4-dihydro-2 H-pyran (syn-2) and anti-2, respectively, both of which were accessible by stereoselective reduction of 2-propionyl-6-methyl-3, 4-dihydro-2 H-pyran (1). Similarly, (-)-forntalin of 91% e. e. was obtained via consecutive enzymatic hydrolysis or acetylation of 2-methoxycarbonyl (5), 2-hydroxymethyl (6), and 2-acetoxymethyl derivative (7) of 2, 6-dimethyl-3, 4-dihydro-2 H-pyran.
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U2 - 10.1246/nikkashi.1993.1162
DO - 10.1246/nikkashi.1993.1162
M3 - Article
AN - SCOPUS:85016521151
SN - 0369-4577
VL - 1993
SP - 1162
EP - 1166
JO - Nippon Kagaku Kaishi / Chemical Society of Japan - Chemistry and Industrial Chemistry Journal
JF - Nippon Kagaku Kaishi / Chemical Society of Japan - Chemistry and Industrial Chemistry Journal
IS - 10
ER -