Synthesis of 4-(1-Naphthyl)-2-Butynoic Acid

Doukas, Harry M.; Wolfe, Winthrop C; Fontaine, Thomas D.

doi:10.1021/jo01368a009

J. Org. Chem.

1954

DOI: 10.1021/jo01368a009

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Synthesis of 4-(1-Naphthyl)-2-Butynoic Acid

Harry M. Doukas¹,

Winthrop C Wolfe²,

Thomas D. Fontaine³

Abstract: The synthesis of a new acetylenic acid, 4-(l-naphthyl)-2-butynoic acid, and some of its derivatives has been described. Infrared data have been used as an aid in establishing its structure.Philadelphia 18, Penna.

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1964

2005

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References 8 publications

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Enantioselective Synthesis and Cytotoxic Evaluation of 4,5-Dihydro-5-[aryl(hydroxy)methyl]-3-methylidenefuran-2(3H)-ones

Janecki

Albrecht

Warzycha

et al. 2005

C&B

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A series of enantiomerically enriched 4,5-dihydro-5-[aryl(hydroxy)methyl]-3-methylidenefuran-2(3H)-ones (8) were synthesized by means of asymmetric Sharpless dihydroxylation of the 2-phosphorylated 5-aryl-pent-4-enoic acids 13, followed by Horner-Wadsworth-Emmons reaction of the resulting furanones 15 (Scheme 2). An enantiomeric excess (ee) of 20-95% was achieved for compounds 8, and their absolute configurations were determined by the Mosher ester method. Cytotoxic evaluation against L-1210 and HL-60 leukemia cell lines revealed that the target compounds 8 are active in the micromolar concentration range (Table 2). Thereby, significant differences in activity between the corresponding enantiomers were observed for the HL-60 cell line.

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Enantioselective Synthesis and Cytotoxic Evaluation of 4,5-Dihydro-5-[aryl(hydroxy)methyl]-3-methylidenefuran-2(3H)-ones

Janecki

Albrecht

Warzycha

et al. 2005

C&B

View full text Add to dashboard Cite

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Über chelatbildende Salicylsäure‐Analoge der Thiophenreihe

Courtin

Class

Erlenmeyer

1964

Helvetica Chimica Acta

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Synthesis of 4-(1-Naphthyl)-2-Butynoic Acid

Abstract: The synthesis of a new acetylenic acid, 4-(l-naphthyl)-2-butynoic acid, and some of its derivatives has been described. Infrared data have been used as an aid in establishing its structure.Philadelphia 18, Penna.

Cited by 2 publications

References 8 publications

Enantioselective Synthesis and Cytotoxic Evaluation of 4,5-Dihydro-5-[aryl(hydroxy)methyl]-3-methylidenefuran-2(3H)-ones

Enantioselective Synthesis and Cytotoxic Evaluation of 4,5-Dihydro-5-[aryl(hydroxy)methyl]-3-methylidenefuran-2(3H)-ones

Über chelatbildende Salicylsäure‐Analoge der Thiophenreihe

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