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1 article(s) from Ward, Jas S

Revisiting the bromination of 3β-hydroxycholest-5-ene with CBr₄/PPh₃ and the subsequent azidolysis of the resulting bromide, disparity in stereochemical behavior

Christian Schumacher,
Jas S. Ward,
Kari Rissanen,
Carsten Bolm and
Mohamed Ramadan El Sayed Aly

Beilstein J. Org. Chem. 2023, 19, 91–99, doi:10.3762/bjoc.19.9

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Figure 1: Chemical structure of three isomeric cholesterols.

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Figure 2: Selected previously described cholesterol derivatives with interesting antibacterial and cytotoxic ...

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Scheme 1: Stereochemical outcome of OH/N₃ transformations under different conditions.

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Figure 3: Top: cholesterol (1) and the less polar product from the Appel reaction, cholesta-3,5-diene (9); bo...

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Figure 4: Top: the more polar product from the Appel reaction 3β-bromocholest-5-ene (4); bottom: X-ray struct...

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Figure 5: Top: 3α-azidocholest-5-ene (5) obtained by treatment of 4 with NaN₃ in DMF; bottom: X-ray crystal s...

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Scheme 2: Mechanistic interpretation of the conversion of cholesterol 1 into diene 9, bromide 4, and azides 5...

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Figure 6: Compounds (next to 4, 5 and 9) to be corrected in refs. [10] and [11]. The respective bonds are highlighted...

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Published 27 Jan 2023

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Revisiting the bromination of 3β-hydroxycholest-5-ene with CBr4/PPh3 and the subsequent azidolysis of the resulting bromide, disparity in stereochemical behavior

Revisiting the bromination of 3β-hydroxycholest-5-ene with CBr₄/PPh₃ and the subsequent azidolysis of the resulting bromide, disparity in stereochemical behavior