TY - JOUR
T1 - A synthesis of (R-recifeiolide by the aid of biochemical reaction as the key-step
AU - Mochizuki, Naoki
AU - Yamada, Hiroshi
AU - Sugai, Takeshi
AU - Ohta, Hiromichi
PY - 1993/7
Y1 - 1993/7
N2 - (R)-Recifeiolide, a naturally occurring macrolactone, was synthesized in optically pure form by the aid of biocatalysts. Lipase-catalyzed lactonization of the racemic precursor afforded the desired compound with a concomitant kinetic resolution. The optically active acyclic precursor could be synthesized by the reduction of corresponding ketone with Pichia farinosa IAM 4682. The yeast reduction proceeded with the anti-Prelog rule, selecting si-face attack on the carbonyl group to give (R)-alcohol with > 95% e.e.
AB - (R)-Recifeiolide, a naturally occurring macrolactone, was synthesized in optically pure form by the aid of biocatalysts. Lipase-catalyzed lactonization of the racemic precursor afforded the desired compound with a concomitant kinetic resolution. The optically active acyclic precursor could be synthesized by the reduction of corresponding ketone with Pichia farinosa IAM 4682. The yeast reduction proceeded with the anti-Prelog rule, selecting si-face attack on the carbonyl group to give (R)-alcohol with > 95% e.e.
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U2 - 10.1016/S0968-0896(00)82105-7
DO - 10.1016/S0968-0896(00)82105-7
M3 - Article
C2 - 8081840
AN - SCOPUS:0027633878
SN - 0968-0896
VL - 1
SP - 71
EP - 75
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
IS - 1
ER -