Reaction of aldehydes with stabilized sulfur ylides. Highly stereoselective synthesis of 2,3-epoxy-amides

Fernández, M. Valpuesta; Durante-Lanes, Patricia; Lopez‐Herrera, F. J.

doi:10.1016/s0040-4020(01)90089-4

Cited by 57 publications

(14 citation statements)

References 13 publications

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“…Fraction 10, a light yellow syrup showed a single spot on TLC and possessed significant antibacterial effect. Its spectral data which were comparable with the literature values, revealed its structure as (3S,4R)-3,4,5-trihydroxypentanoic acid-1,4-lactone (1) (Fernandez et al, 1990). In fraction 13, an insoluble matter settled down which was filtered affording soluble (13F) and insoluble (13R) portions, both of which showed weak activity.…”

Section: Extraction Of Stem Of Polyalthia Longifolia Var Pendulasupporting

confidence: 73%

“…This observation revealed that free hydroxyls in (1) are necessary for its activity. The lactone (1) had been synthesized from various methods (Fernandez et al, 1990) and is commercially available (Doyle et al, 1999), however, no investigation about its antimicrobial spectrum has ever been conducted. It is the first report of the isolation of this compound from the family Annonaceae, earlier it was obtained only twice, from fennel (Kitajima et al, 1999) and ajowan (Ishikawa et al, 2001), which belong to family Umbelliferae.…”

Section: Resultsmentioning

confidence: 99%

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Evaluation of the antimicrobial property of Polyalthia longifolia var. pendula: isolation of a lactone as the active antibacterial agent from the ethanol extract of the stem

Faizi

Mughal

Khan

et al. 2003

Phytotherapy Research

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Bioassay guided fractionation of the ethanolic extract of Polyalthia longifolia var. pendula stem, which showed promising antibacterial activity against thirteen Gram-positive and nine Gram-negative organisms, furnished (3S,4R)-3,4,5-trihydroxypentanoic acid-1,4-lactone (1) as the active principle. The structure of (1) was established by UV, IR, mass, 1H and 13C NMR as well as 2D NMR spectral studies and the formation of its acetate (1a). On acetylation activity of (1) was markedly reduced. It is synthetically well known and only recently isolated from two plants, however, its antimicrobial activity was not reported earlier. The extract, fractions and pure compounds did not show any remarkable activity against fungi and Mycobacterium fortuitum, and M. smegmatis.

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Section: Extraction Of Stem Of Polyalthia Longifolia Var Pendulasupporting

confidence: 73%

Section: Resultsmentioning

confidence: 99%

Evaluation of the antimicrobial property of Polyalthia longifolia var. pendula: isolation of a lactone as the active antibacterial agent from the ethanol extract of the stem

Faizi

Mughal

Khan

et al. 2003

Phytotherapy Research

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“…The presence of a strong cross peak between H-3 and H-5 in the NOESY spectrum suggested that H-3 and H-4 were at the opposite side of the -lactone ring. This was supported by the close similarity of the 1 H NMR coupling constant between H-3 and H-4 of 1 to that of (3S,4R)-3,4,5-trihydroxypentanoic acid 1,4-lactone [4]. Comparison of the 13 C NMR chemical shift of C-5 and the 1 H NMR coupling constant between H-4 and H-5 of 1 with those of the four stereoisomers of 5-hydroxy-4-decanolide [5] indicated that the relationship between C-4 and C-5 in 1 was erythro.…”

Section: Resultsmentioning

confidence: 70%

Polyporolide, a new acetogenin from the mycelial culture of a Polyporus fungus

Chen

Huang

et al. 2006

Natural Product Research

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“…Interestingly, the amide-stabilized ylide 6 , for which betaine formation is expected to be even more reversible, has been reported to give exclusively the trans epoxide 9 but again as an 86: 14 ratio of diastereoisomers. [ 7 ]…”

Section: Resultsmentioning

confidence: 99%

Reagent controlled addition of chiral sulfur ylides to chiral aldehydes

Aggarwal¹,

Bi²

2005

Beilstein J. Org. Chem.

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The degree of reagent and substrate control in the reaction of chiral sulfur ylides with chiral aldehydes has been investigated. Specifically, the reactions of the two enantiomers of the chiral benzyl sulfonium salt 1 with glyceraldehyde acetonide were studied in detail. Of the two new stereogenic centers created, it was found that the C 1 stereochemistry was largely controlled by the reagent, whereas control at the C 2 center was dependent on the aldehyde used. In one case, the trans isomer was produced via reversible formation of the intermediate betaine, whereas in the alternative case, the C 2 center was under Felkin Anh/Cornforth control through non-reversible formation of the betaine. Thus, the aldehyde stereocenter influenced the degree of reversibility in betaine formation, which impacted on the stereocontrol at the C 2 position.

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Reaction of aldehydes with stabilized sulfur ylides. Highly stereoselective synthesis of 2,3-epoxy-amides

Cited by 57 publications

References 13 publications

Evaluation of the antimicrobial property of Polyalthia longifolia var. pendula: isolation of a lactone as the active antibacterial agent from the ethanol extract of the stem

Evaluation of the antimicrobial property of Polyalthia longifolia var. pendula: isolation of a lactone as the active antibacterial agent from the ethanol extract of the stem

Polyporolide, a new acetogenin from the mycelial culture of a Polyporus fungus

Reagent controlled addition of chiral sulfur ylides to chiral aldehydes

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