A synthesis of (−)-sitophilate by utilizing yeast-mediated reduction of an enol ester

Sugai, Takeshi; Sakuma, Daisuke; Kobayashi, Naoki; Ohta, Hiroyuki

doi:10.1016/s0040-4020(01)89726-x

Cited by 17 publications

(3 citation statements)

References 17 publications

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“…1) (23). For this type biotransformation, the microbial conversion of enol ester using Pichia farinosa has been reported (24). The microorganisms that have the ability to catalyze the conversion of 12 into (2S,3S)-11, with excellent enantioselectivity, are summarized in Table 3.…”

Section: Microbial Conversion Of 3-acetoxy-2-(4-methoxyphenyl)-15-bementioning

confidence: 99%

Diltiazem Synthesis, Microbial Asymmetric Reduction

Nishida

Shibatani

2010

Encyclopedia of Industrial Biotechnology

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Section: Microbial Conversion Of 3-acetoxy-2-(4-methoxyphenyl)-15-bementioning

confidence: 99%

Diltiazem Synthesis, Microbial Asymmetric Reduction

Nishida

Shibatani

2010

Encyclopedia of Industrial Biotechnology

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“…Its male-produced aggregation pheromone sitophilate (41) was isolated and identified as l'-ethylpropyl (2S)-methyl-(3R)-hydroxypentanoate [182]. Sugai et al [183] synthesized 41 through the reduction of the corresponding enol ester by growing cells of the yeast Pichia farinosa IAM 4682.…”

Section: Synthesis Of Acidic Pheromones and Related Compoundsmentioning

confidence: 99%

Biocatalysis Applied to the Synthesis of Pheromones

Aleu¹,

Bustillo²,

Hernández-Galán³

et al. 2007

COC

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The application of biologically derived catalysts to the synthesis of agrochemicals has become increasingly popular in recent years. In most cases, the aim of using a biotransformation is either to introduce chirality into the molecule, to achieve a regioselective functionalization, or to selectively convert a functional group among other groups with similar reactivity. Pheromones, which have recently been commercialized as agrochemicals, are generally used in enantiopure forms with their intentional mixtures. Since they are usually highly effective, only very small quantities are needed to achieve the desired activity. This review, with approximately 200 references covering the period previous to December 2004, describes various efficient means of preparing optically pure pheromones and their precursors with the aid of isolated enzymes and microorganisms serving as catalysts.

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“…Several racemic or asymmetric syntheses, involving several steps with overall yields ranging from moderate to low, have been reported. [22][23][24][25][26][27][28] Most of them did not lead to the required syn isomer, requiring an additional Mitsunobu reaction in order to force a configurational inversion at the centre bearing the hydroxy group. 29 Herein, we report a simple synthesis of (±)-sitophilate in two steps: addition of propanal to the lithium enediolate of propanoic acid and subsequent esterification with 3-pentanol under standard Fischer conditions (Scheme 1).…”

Section: Figurementioning

confidence: 99%