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The synthesis of 11-aza pregnane derivatives Sood, Rattan Sagar
Abstract
The Beckmann rearrangement of the oxime of 11-oxo-⍺, 20-dihydroxy-C-nor pregnane (54) provided the corresponding lactam (56). Oxidation of the latter with Jones reagent furnished the 3-keto-alcohol (57), which upon its conversion to the acetate derivative (58) followed by bromination and dehydrobromination yielded ll-aza-20-acetoxy-pregn-4-ene-3,12-dione (60). Hydrolysis of the latter to the ∆⁴ -3-keto alcohol (62) followed by oxidation furnished the desired ll-aza-pregn-4-ene-3,12,20-trione (63). The synthetic sequence provides the first examples of ll-aza steroid analogues in which ring C is a six membered and ring A possesses the ∆⁴-3-keto moiety.
Item Metadata
| Title |
The synthesis of 11-aza pregnane derivatives
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| Creator | |
| Publisher |
University of British Columbia
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| Date Issued |
1967
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| Description |
The Beckmann rearrangement of the oxime of 11-oxo-⍺, 20-dihydroxy-C-nor pregnane (54) provided the corresponding lactam (56). Oxidation of the latter with Jones reagent furnished the 3-keto-alcohol (57), which upon its conversion to the acetate derivative (58) followed by bromination and dehydrobromination yielded ll-aza-20-acetoxy-pregn-4-ene-3,12-dione (60). Hydrolysis of the latter to the ∆⁴ -3-keto alcohol (62) followed by oxidation furnished the desired ll-aza-pregn-4-ene-3,12,20-trione (63). The synthetic sequence provides the first examples of ll-aza steroid analogues in which ring C is a six membered and ring A possesses the ∆⁴-3-keto moiety.
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| Genre | |
| Type | |
| Language |
eng
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| Date Available |
2011-07-15
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| Provider |
Vancouver : University of British Columbia Library
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| Rights |
For non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use.
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| DOI |
10.14288/1.0061892
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| URI | |
| Degree (Theses) | |
| Program (Theses) | |
| Affiliation | |
| Degree Grantor |
University of British Columbia
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| Campus | |
| Scholarly Level |
Graduate
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| Aggregated Source Repository |
DSpace
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Rights
For non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use.