Kilogram-Scale Synthesis of 11β-Hydroxyandrosterone
Hossay Abas
1
,
Peter Blencowe
1
,
Ellen MacDonald
1
,
Emma Stanway
1
,
Eric P. A. Talbot
2
,
Haiyang Wang
3
,
Morag Watson
1
,
Jin Zhang
3
,
Lucy A Harwood
1
1
Cancer Research Horizons, Babraham Research Campus, Cambridge CB22 3AT, U.K.
|
2
Pharmaron U.K., Innovation Park, Hoddesdon EN11 9FH, U.K.
|
3
Pharmaron Beijing Co., Ltd., No.6 Taihe Road, Beijing 100176, China
|
Publication type: Journal Article
Publication date: 2024-05-06
scimago Q1
wos Q1
SJR: 0.865
CiteScore: 5.4
Impact factor: 3.5
ISSN: 10836160, 1520586X
Abstract
This article describes a robust and large-scale synthesis of the ketosteroid building block 11β-hydroxyandrosterone (2) from cheap and readily available hydrocortisone (1). The initial discovery route, which was conducted on a gram scale and achieved a 3–6% yield over eight steps, is also described. Key to the route redesign was the incorporation of two stereoselective steps setting the desired 5α-H and 3α-OH chiral centers and optimization to minimize chromatographic purification. The process route was then conducted at the kilogram scale and achieved a 21–28% yield over four steps.
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Citations from 2024:
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(100%)
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Abas H. et al. Kilogram-Scale Synthesis of 11β-Hydroxyandrosterone // Organic Process Research and Development. 2024. Vol. 28. No. 7. pp. 2692-2701.
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Abas H., Blencowe P., MacDonald E., Stanway E., Talbot E. P. A., Wang H., Watson M., Zhang J., Harwood L. A. Kilogram-Scale Synthesis of 11β-Hydroxyandrosterone // Organic Process Research and Development. 2024. Vol. 28. No. 7. pp. 2692-2701.
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RIS
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TY - JOUR
DO - 10.1021/acs.oprd.4c00084
UR - https://pubs.acs.org/doi/10.1021/acs.oprd.4c00084
TI - Kilogram-Scale Synthesis of 11β-Hydroxyandrosterone
T2 - Organic Process Research and Development
AU - Abas, Hossay
AU - Blencowe, Peter
AU - MacDonald, Ellen
AU - Stanway, Emma
AU - Talbot, Eric P. A.
AU - Wang, Haiyang
AU - Watson, Morag
AU - Zhang, Jin
AU - Harwood, Lucy A
PY - 2024
DA - 2024/05/06
PB - American Chemical Society (ACS)
SP - 2692-2701
IS - 7
VL - 28
SN - 1083-6160
SN - 1520-586X
ER -
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BibTex (up to 50 authors)
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@article{2024_Abas,
author = {Hossay Abas and Peter Blencowe and Ellen MacDonald and Emma Stanway and Eric P. A. Talbot and Haiyang Wang and Morag Watson and Jin Zhang and Lucy A Harwood},
title = {Kilogram-Scale Synthesis of 11β-Hydroxyandrosterone},
journal = {Organic Process Research and Development},
year = {2024},
volume = {28},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://pubs.acs.org/doi/10.1021/acs.oprd.4c00084},
number = {7},
pages = {2692--2701},
doi = {10.1021/acs.oprd.4c00084}
}
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MLA
Copy
Abas, Hossay, et al. “Kilogram-Scale Synthesis of 11β-Hydroxyandrosterone.” Organic Process Research and Development, vol. 28, no. 7, May. 2024, pp. 2692-2701. https://pubs.acs.org/doi/10.1021/acs.oprd.4c00084.
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