A synthesis of (R)-recifeiolide by the aid of biochemical reaction as the key-step.
(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.
Mochizuki
N
N
Department of Chemistry, Keio University, Yokohama, Japan.
Yamada
H
H
Sugai
T
T
Ohta
H
H
D000164:Acremonium / Q000378:metabolism*; D002384:Catalysis; D004952:Esters; D007659:Ketones / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis*; D008049:Lipase / Q000378:metabolism; D010084:Oxidation-Reduction; D010843:Pichia; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
D004952:Esters; D007659:Ketones; D007783:Lactones; C089339:recifeiolide; D008049:Lipase