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Volumn , Issue 13, 2007, Pages 2133-2135

Synthesis of novel steroidal hydroxy cyclohexenone

Author keywords

Borohydride reduction; Chemoselectivity; Diels Alder reaction; p benzoquinone; Steroid

Indexed keywords

1,4 BENZOQUINONE; 2 CYCLOHEXENONE; 4 HYDROXY 2 CYCLOHEXENONE; SODIUM BOROHYDRIDE; STEROID; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; GEOMETRY;

EID: 34548170987 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-984898 Document Type: Article

Times cited : (3)

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- Procedure of Diels-Alder Reaction for the Synthesis of Cycloadduct 5 p-Benzoquinone (1 mmol) and steroidal diene 3 (1 mmol) in hexane (40 mL) were refluxed for 8 h and allowed to cool to r.t. The solvent was removed in vacuo to give 5, which was used in the next step without purification. Procedure for Sodium Borohydride Reduction of Cycloadduct 5 Sodium borohydride (3.83 mmol) was added in small portions to a solution of 5 (1 mmol) and CeCl3 (1.79 mmol) in MeOH-CH2Cl 2 (9 mL, 3 mL) at 0°C. After the addition was complete, the mixture was stirred at 0°C for 2 h and then at r.t. for 1 h. Solvent was removed in vacuo and residue was diluted with H2O and extracted thrice with CH2Cl2. The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. To this compound in CH2Cl2 was added 0.5 mL HCl. The
- +: 489.2617; found: 489.2610.

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22
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- 5, crystal system, space group: monoclinic, P21; some of the important bond lengths: O(1)-C(2), 1.330 (5); O(1)-C(3), 1.452 (4); O(2)-C(2), 1.213 (5); O(3)-C(22), 1.220 (5); O(4)-C(26), 1.223 (5); O(5)-C(29), 1.438 (5); O(5)-H(5). 0.8200; C(1)-C(2), 1.498(6).
- 5, crystal system, space group: monoclinic, P21; some of the important bond lengths: O(1)-C(2), 1.330 (5); O(1)-C(3), 1.452 (4); O(2)-C(2), 1.213 (5); O(3)-C(22), 1.220 (5); O(4)-C(26), 1.223 (5); O(5)-C(29), 1.438 (5); O(5)-H(5). 0.8200; C(1)-C(2), 1.498(6).

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