A sterospecific synthesis of 7α-hydroxycholesterol

The five step synthesis of 7α-hydroxycholesterol utilizes the solvolysis of 7α-bromocholesterol benzoate with potassium acetate in acetic acid as the key step in controlling the stereospecificity of the reaction sequence. This reaction yields 7α-acetoxycholesterol benzoate with retention of configur...

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Bibliographic Details
Main Authors:	D B Johnson, L Lack
Format:	Article
Language:	English
Published:	Elsevier 1976-01-01
Series:	Journal of Lipid Research
Subjects:	7α-hydroxycholesterol synthesis 7α-bromocholesterol
Online Access:	http://www.sciencedirect.com/science/article/pii/S002222752037022X

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spelling	doaj-70de37b1ec604173a5b46c617fdf5db22021-04-24T05:49:56ZengElsevierJournal of Lipid Research0022-22751976-01-011719193A sterospecific synthesis of 7α-hydroxycholesterolD B Johnson0L Lack1Department of Physiology and Pharmacology, Duke University LIledical Center, Box 3186 Durham, North Carolina 27710Department of Physiology and Pharmacology, Duke University LIledical Center, Box 3186 Durham, North Carolina 27710The five step synthesis of 7α-hydroxycholesterol utilizes the solvolysis of 7α-bromocholesterol benzoate with potassium acetate in acetic acid as the key step in controlling the stereospecificity of the reaction sequence. This reaction yields 7α-acetoxycholesterol benzoate with retention of configuration at position seven. The diester is readily reduced with lithium aluminum to 7α-hydroxycholesterol.http://www.sciencedirect.com/science/article/pii/S002222752037022X7α-hydroxycholesterolsynthesis7α-bromocholesterol
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	D B Johnson L Lack
spellingShingle	D B Johnson L Lack A sterospecific synthesis of 7α-hydroxycholesterol Journal of Lipid Research 7α-hydroxycholesterol synthesis 7α-bromocholesterol
author_facet	D B Johnson L Lack
author_sort	D B Johnson
title	A sterospecific synthesis of 7α-hydroxycholesterol
title_short	A sterospecific synthesis of 7α-hydroxycholesterol
title_full	A sterospecific synthesis of 7α-hydroxycholesterol
title_fullStr	A sterospecific synthesis of 7α-hydroxycholesterol
title_full_unstemmed	A sterospecific synthesis of 7α-hydroxycholesterol
title_sort	sterospecific synthesis of 7α-hydroxycholesterol
publisher	Elsevier
series	Journal of Lipid Research
issn	0022-2275
publishDate	1976-01-01
description	The five step synthesis of 7α-hydroxycholesterol utilizes the solvolysis of 7α-bromocholesterol benzoate with potassium acetate in acetic acid as the key step in controlling the stereospecificity of the reaction sequence. This reaction yields 7α-acetoxycholesterol benzoate with retention of configuration at position seven. The diester is readily reduced with lithium aluminum to 7α-hydroxycholesterol.
topic	7α-hydroxycholesterol synthesis 7α-bromocholesterol
url	http://www.sciencedirect.com/science/article/pii/S002222752037022X
work_keys_str_mv	AT dbjohnson asterospecificsynthesisof7ahydroxycholesterol AT llack asterospecificsynthesisof7ahydroxycholesterol AT dbjohnson sterospecificsynthesisof7ahydroxycholesterol AT llack sterospecificsynthesisof7ahydroxycholesterol
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A sterospecific synthesis of 7α-hydroxycholesterol

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