(1S,3S)-1-tert-Butyldiphenylsiloxy-3-hydroxy-3-isopropenyl-1,2,3,4-tetrahydronaphthalene

Fan, Eric; Lowary, Todd L.; Ferguson, Michael J.

doi:10.1107/s1600536805037736

Cited by 2 publications

(4 citation statements)

References 9 publications

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“…An X‐ray crystallographic investigation was reported for compound 3 , an intermediate in the enantioselective synthesis of 4 17. The crystal structure showed that the isopropenyl group is oriented trans to, and the OH group is cis to, the OTBDPS group, and that the absolute configuration for the C1 and C3 stereogenic centers is SS 17. Our conclusion on the absolute configuration of 4 is consistent with the result from this X‐ray crystallographic study.…”

Section: Resultssupporting

confidence: 88%

“…The calculated VA and VCD spectra of M4a are directly compared to the experimental data in Figure 4, showing good agreement in the band positions, the signs, and the relative intensities. An X‐ray crystallographic investigation was reported for compound 3 , an intermediate in the enantioselective synthesis of 4 17. The crystal structure showed that the isopropenyl group is oriented trans to, and the OH group is cis to, the OTBDPS group, and that the absolute configuration for the C1 and C3 stereogenic centers is SS 17.…”

Section: Resultsmentioning

confidence: 99%

“…These compounds were assayed against several cancer cell lines, with some compounds showing modest cytotoxicity 16. In the preparation of these compounds, the relative and absolute stereochemistry of 2 , the synthetic precursor of 1 , was inferred based on the similarity of the synthetic route and NMR data compared with compound 3 , whose crystal structure had been obtained 17. To confirm the stereochemical configuration of 2 , more experimental evidence is necessary due to the inability to obtain a crystal structure of this molecule or related derivatives.…”

Section: Introductionmentioning

confidence: 99%

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Determination of the absolute configurations of synthetic daunorubicin analogues using vibrational circular dichroism spectroscopy and density functional theory

Yang¹,

Tran²,

Fan³

et al. 2010

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The absolute configurations of three synthesized anthracycline analogues have been determined using vibrational circular dichroism (VCD) spectroscopy and the density functional theory (DFT) calculations. The experimental VCD spectra of the three compounds have been measured for the first time in the film state, prepared from their CDCl(3) solutions. Conformational searches for the monomers and some dimers of the three compounds have been performed at the DFT level using the B3LYP functional and the 6-311G** and 6-311++G** basis sets. The corresponding vibrational absorption and VCD spectra have been calculated. The good agreement between the experimental and the calculated spectra allows one to assign the absolute configurations of the three compounds with high confidence. In addition, the dominant conformers of the three compounds have also been identified.

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Section: Resultssupporting

confidence: 88%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Determination of the absolute configurations of synthetic daunorubicin analogues using vibrational circular dichroism spectroscopy and density functional theory

Yang¹,

Tran²,

Fan³

et al. 2010

Chirality

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“…Separation of these diastereomers by chromatography afforded pure 24 , a crystalline compound. A single-crystal X-ray study verified that the isopropenyl and siloxy groups were on opposite sides of the molecule …”

Section: Resultsmentioning

confidence: 94%

Synthesis of Daunorubicin Analogues Containing Truncated Aromatic Cores and Unnatural Monosaccharide Residues

2007

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The anthracycline antibiotics daunorubicin and doxorubicin have been used widely as anticancer drugs, but their cardiotoxicity limits their clinical use. We describe here the preparation of a small panel of daunorubicin analogues in which the anthraquinone core is replaced with simpler aromatic moieties that lack a quinone functionality. The targets consist of a functionalized 1,2,3,4-tetrahydro-naphthalene or 1,2,3,4-tetrahydro-anthracene core bound to one of three monosaccharides: daunosamine, acosamine, or 4-amino-2,3,6-trideoxy-l-threo-hexopyranose. Key steps in the synthesis included an enantioselective ring opening of benzo-fused norbornene derivatives for the preparation of the core structures and the use of silver hexafluorophosphate-promoted thioglycoside activation in the glycosylation of these cores. Evaluation of these compounds against the MCF-7 cancer cell line demonstrated that the identity of the carbohydrate moiety appeared to have little influence on the cytotoxicity. Moreover, the analogues with the 1,2,3,4-tetrahydro-naphthalene core showed no cytotoxicity, while those possessing the 1,2,3,4-tetrahydro-anthracene moiety were more active. The IC50 values for the latter group of compounds were in the range of 94-134 microM, compared to 17 microM for doxorubicin and 5 microM for daunorubicin.

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(1S,3S)-1-tert-Butyldiphenylsiloxy-3-hydroxy-3-isopropenyl-1,2,3,4-tetrahydronaphthalene

Cited by 2 publications

References 9 publications

Determination of the absolute configurations of synthetic daunorubicin analogues using vibrational circular dichroism spectroscopy and density functional theory

Determination of the absolute configurations of synthetic daunorubicin analogues using vibrational circular dichroism spectroscopy and density functional theory

Synthesis of Daunorubicin Analogues Containing Truncated Aromatic Cores and Unnatural Monosaccharide Residues

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