Chemoenzymatic formal synthesis of (S)-(−)-phosphonotrixin

Chênevert, Robert; Simard, Mathieu; Bergeron, Jérôme; Dasser, Mohammed

doi:10.1016/j.tetasy.2004.04.046

Cited by 16 publications

(9 citation statements)

References 8 publications

(3 reference statements)

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“…Chemoenzymatic synthesis of (18S)-variabilin. organism Saccharotrix sp., was reported recently [159]. Retrosynthetic analysis of the phosphonotrixin structure suggested that prochiral triol 23 might serve as a suitable substrate for an enzyme-catalyzed desym-metrization, Fig.…”

Section: Prochiral Substratementioning

confidence: 75%

Stereoselective Enzymatic Acylations (Transesterifications)

Chênevert¹,

Pelchat²,

Jacques

2006

COC

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Section: Prochiral Substratementioning

confidence: 75%

Stereoselective Enzymatic Acylations (Transesterifications)

Chênevert¹,

Pelchat²,

Jacques

2006

COC

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“…Since the reaction does not take place at the chiral secondary center itself, observed enantioselectivities are usually low or enantioselectivity was not observed at all [ 22 ]. Usually this kind of reaction proceeds with very low (or none) enantioselectivity, although some specific classes of primary alcohol can be acylated with high enantioselectivity by mean of lipase catalysis [ 23 , 24 , 25 ]. The phenomenon that diols are inferior substrates than their corresponding monoacylated derivatives in lipase catalyzed transesterification is generally known.…”

Section: Resultsmentioning

confidence: 99%

Lipases as Tools in the Synthesis of Prodrugs from Racemic 9-(2,3-Dihydroxypropyl)adenine

et al. 2012

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Lipases from Geotrichum candidum 4013 (extracellular lipase and cell-bound lipase) were immobilized by adsorption on chitosan beads. The enzyme preparations were tested in the synthesis of ester prodrugs from racemic 9-(2,3-dihydroxypropyl)adenine in dimethylformamide with different vinyl esters (acetate, butyrate, decanoate, laurate, palmitate). The transesterification activities of these immobilized enzymes were compared with commercially available lipases (lipase from hog pancreas, Aspergillus niger, Candida antarctica, Pseudomonas fluorescens). Lipase from Candida antarctica was found to be the most efficient enzyme regarding chemical yield of the desired products, while transesterification by lipase from Aspergillus niger resulted in lower yields.

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“…[35] A final attempt was performed with chlorohydrin 37: Exposure of this compound to TBSOTf in the presence of 2,6-lutidine provided the corresponding TBS ether 38 in 50 % yield, which was then treated with sodium hydroxide without success (Scheme 10). [36] Scheme 10. Silylation of compound 37.…”

Section: Resultsmentioning

confidence: 99%

Towards the Synthesis of the 4,19‐Diol Derivative of (–)‐Mycothiazole: Synthesis of a Potential Key Intermediate

Batt

Fache

2011

Eur J Org Chem

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The synthesis of a potential key intermediate for the synthesis of the 4,19‐diol derivative of (–)‐mycothiazole using convergent strategies is described in this paper. Several approaches have been tested, including cross metathesis and a Julia–Kocienski olefination. Finally, the formation of the 1,1‐dialkyl‐1,2‐ethanediol motif through C4–C5 bond construction was realized by nucleophilic addition of a vinyl iodide derivative to a keto ester after halogen/lithium exchange followed by reduction of the resulting hydroxy ester.

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Chemoenzymatic formal synthesis of (S)-(−)-phosphonotrixin

Cited by 16 publications

References 8 publications

Stereoselective Enzymatic Acylations (Transesterifications)

Stereoselective Enzymatic Acylations (Transesterifications)

Lipases as Tools in the Synthesis of Prodrugs from Racemic 9-(2,3-Dihydroxypropyl)adenine

Towards the Synthesis of the 4,19‐Diol Derivative of (–)‐Mycothiazole: Synthesis of a Potential Key Intermediate

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