Microbiological synthesis of variously protected L-glyceraldehydes in high optical purity

Guanti, Giuseppe; Banfi, Luca; Narisano, Enrica

doi:10.1016/s0040-4039(00)84846-7

Cited by 60 publications

(25 citation statements)

References 9 publications

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“…[2] [9] [10] It should be stressed that both enantiomers of a given THYM* or of a given BHYMA* are accessible in similar yield and with the same number of steps starting from a given enantiomer of 19, simply by reversing the order of protecting group introduction. This property (enantiodivergency) [11] is typical of all the building blocks possessing a latent plane of symmetry, and in our case adds further stereochemical flexibility. The last step in preparation of aldehydes 22 involved ozonolysis of the double bond.…”

Section: Preparationmentioning

confidence: 62%

“…104) structurally similar to those achievable by stereoselective nucleophilic addition to BHYMA*. After a deep investigation, [33] on varying the protecting groups and the reagents, we eventually found two methods yielding the regioisomers 104 in excellent regioselectivity, that is the combination of DIBALH and BF 3 •Et 2 O, and the system MgI 2 -nBu 3 SnH. [34] The latter method proceeds through an intermediate iodohydrin, that can be also isolated in the absence of tributyltin hydride.…”

Section: Elaborations Through Olefination Followed By Electrophilic Amentioning

confidence: 85%

“…All the steps proceeded in high yield. Scheme 8 Another example is depicted in Scheme 9, which illustrates the enantiodivergent [11] preparation, starting from a single enantiomer of monoacetate 19, of both enantiomers of the "open-chain" nucleotide analogue 39. [16] These compounds are interesting as potential antiviral agents.…”

Section: Elaborations Not Involving Creation Of Additional Stereocentersmentioning

confidence: 99%

“…This property has been defined as diastereodivergency. [11] Since also both enantiomers of starting BHYMA* are enantiodivergently accessible, all four stereoisomers of a given protected 2-hydroxymethyl-1,3-alkanediol can be prepared (double stereodivergency) [11] starting from a single enantiomer of monoacetate 19.…”

Section: Elaborations Through Diastereoselective Additions To Bhyma* mentioning

confidence: 99%

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Asymmetrized Tris(hydroxymethyl)methane and Related Synthons: Enantioselective Preparation and Synthetic Applications

Banfi¹,

Guanti²

1998

Eur. J. Org. Chem.

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Asymmetrized tris(hydroxymethyl)methane (THYM*) is a new chiral building block easily accessible in both enantiomeric forms by a chemoenzymatic methodology. The presence of three synthetically equivalent masked hydroxymethyl groups and a high degree of latent symmetry (C3v) makes this synthon very versatile in synthetic applications. This review describes its preparation and a series of elaborations (with particular enphasis on the diastereoselective generation of additional chiral centers) leading to advanced intermediated for the preparation of biologically active compounds.

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Section: Preparationmentioning

confidence: 62%

Section: Elaborations Through Olefination Followed By Electrophilic Amentioning

confidence: 85%

Section: Elaborations Not Involving Creation Of Additional Stereocentersmentioning

confidence: 99%

Section: Elaborations Through Diastereoselective Additions To Bhyma* mentioning

confidence: 99%

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Asymmetrized Tris(hydroxymethyl)methane and Related Synthons: Enantioselective Preparation and Synthetic Applications

Banfi¹,

Guanti²

1998

Eur. J. Org. Chem.

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“…The seleno moiety was unstable to the reduction conditions and was recovered as diphenyldiselenide. The a-seleno ketone without the yeast was stable in different buffered solutions, which leads us to think that the fermenting yeast is somehow interacting with the seleno moiety.4 To our knowledge, this is the first report of such an observation, since a-dithianyl ketones and P-thianyl ketones have been reduced with yeast without reported troubles (8,14).…”

Section: Introductionmentioning

confidence: 95%

Optically pure (S)-cyclopent-2-en-1-ol and (S)-3-methoxycyclopentene

Wahhab¹,

Tavares²,

Rauk³

1990

Can. J. Chem.

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Optically pure (S)-cyclopent-2-en-1-ol, [Formula: see text] (c 1.1, CHCl3), and (S)-3-methoxycyclopentene, [Formula: see text] (c 3.86, n-hexane), were prepared from ethyl (1R,2S)-2-hydroxycyclopentanecarboxylate, which is readily available by yeast reduction of ethyl 2-oxocyclopentanecarboxylate. The optical purity of the alcohol was determined from its Mosher ester, and that of the ether by gas chromatography using a Ni-4-Pin column. Keywords: (S)-cyclopent-2-en-1-ol, (S)-3-methoxycyclopentene.

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Quantitative structure-enantioselectivity relationships using neural networks. Bioconversion of carbonyl compounds using baker's yeast

Zakarya

Farhaoui

Fkih‐Tetouani³

1996

J. Phys. Org. Chem.

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Quantitative structure-enantioselectivity relationships were studied for the reduction of a set of 73 carbonyl compounds with bakers yeast. The established model, using a neural network, allowed the prediction of the reduction selectivity (% S enantiomer) with success. The correlation coefficient between the observed and calculated %S was 0.99. The model was also used to predict the enantioselectivity of the reduction of adiketones using bakers yeast and different microorganisms.

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Microbiological synthesis of variously protected L-glyceraldehydes in high optical purity

Cited by 60 publications

References 9 publications

Asymmetrized Tris(hydroxymethyl)methane and Related Synthons: Enantioselective Preparation and Synthetic Applications

Asymmetrized Tris(hydroxymethyl)methane and Related Synthons: Enantioselective Preparation and Synthetic Applications

Optically pure (S)-cyclopent-2-en-1-ol and (S)-3-methoxycyclopentene

Quantitative structure-enantioselectivity relationships using neural networks. Bioconversion of carbonyl compounds using baker's yeast

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