Synthesis of Corticoids from 9α-Hydroxyandrost-4-ene-3,17-dione
Publication
, Journal Article
Carruthers, NI; Garshasb, S; McPhail, AT
Published in: Journal of Organic Chemistry
January 1, 1992
The synthesis of 17α,21-bis(acetyloxy)-16β-methylpregna-4,9(11)-diene-3,20-dione (24) from the sterol-derived 9α-hydroxyandrost-4-ene-3,17-dione (1) has been completed. The key steps in the synthesis are 16β-methylation and conversion of the 17-ketone to 17β-cyanohydrin 11. Elaboration of 11 to 9α-hydroxy-16β-methylpregn-4-ene-3,20-dione (15) followed by 21-acetoxylation and simultaneous introduction of 9,11-unsaturation and 17α-acetoxylation gave 24. © 1992, American Chemical Society. All rights reserved.
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Published In
Journal of Organic Chemistry
DOI
EISSN
1520-6904
ISSN
0022-3263
Publication Date
January 1, 1992
Volume
57
Issue
3
Start / End Page
961 / 965
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry
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Carruthers, N. I., Garshasb, S., & McPhail, A. T. (1992). Synthesis of Corticoids from 9α-Hydroxyandrost-4-ene-3,17-dione. Journal of Organic Chemistry, 57(3), 961–965. https://doi.org/10.1021/jo00029a032
Carruthers, N. I., S. Garshasb, and A. T. McPhail. “Synthesis of Corticoids from 9α-Hydroxyandrost-4-ene-3,17-dione.” Journal of Organic Chemistry 57, no. 3 (January 1, 1992): 961–65. https://doi.org/10.1021/jo00029a032.
Carruthers NI, Garshasb S, McPhail AT. Synthesis of Corticoids from 9α-Hydroxyandrost-4-ene-3,17-dione. Journal of Organic Chemistry. 1992 Jan 1;57(3):961–5.
Carruthers, N. I., et al. “Synthesis of Corticoids from 9α-Hydroxyandrost-4-ene-3,17-dione.” Journal of Organic Chemistry, vol. 57, no. 3, Jan. 1992, pp. 961–65. Scopus, doi:10.1021/jo00029a032.
Carruthers NI, Garshasb S, McPhail AT. Synthesis of Corticoids from 9α-Hydroxyandrost-4-ene-3,17-dione. Journal of Organic Chemistry. 1992 Jan 1;57(3):961–965.
Published In
Journal of Organic Chemistry
DOI
EISSN
1520-6904
ISSN
0022-3263
Publication Date
January 1, 1992
Volume
57
Issue
3
Start / End Page
961 / 965
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry