Stereoselectivity of sodium borohydride reduction of saturated steroidal ketones utilizing conditions of Luche reduction
A series of keto steroids were reduced with sodium borohydride in the presence of cerium(III) chloride or samarium(III) iodide (Luche reduction). The ratios of axial and equatorial alcohols were determined by HPLC and the results were compared with those obtained by a standard sodium borohydride red...
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| Veröffentlicht in: | Steroids 2010-10, Vol.75 (10), p.721-725 |
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| creator | Šťastná, Eva Černý, Ivan Pouzar, Vladimír Chodounská, Hana |
| description | A series of keto steroids were reduced with sodium borohydride in the presence of cerium(III) chloride or samarium(III) iodide (Luche reduction). The ratios of axial and equatorial alcohols were determined by HPLC and the results were compared with those obtained by a standard sodium borohydride reduction. The best results were obtained with the 2-keto derivative
1, 7-keto derivatives
5 and
6, and 12-keto derivative
8 where the cerium(III) ion addition resulted in the inversion of the axial/equatorial ratios. The Luche reduction of the 20-keto derivative
11 improved the proportion of the (20
S)-alcohol in a mixture of (20
S)/(20
R) alcohols up to 35% from 5% in a standard sodium borohydride reduction. |
| doi_str_mv | 10.1016/j.steroids.2010.04.010 |
| format | Article |
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1, 7-keto derivatives
5 and
6, and 12-keto derivative
8 where the cerium(III) ion addition resulted in the inversion of the axial/equatorial ratios. The Luche reduction of the 20-keto derivative
11 improved the proportion of the (20
S)-alcohol in a mixture of (20
S)/(20
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1, 7-keto derivatives
5 and
6, and 12-keto derivative
8 where the cerium(III) ion addition resulted in the inversion of the axial/equatorial ratios. The Luche reduction of the 20-keto derivative
11 improved the proportion of the (20
S)-alcohol in a mixture of (20
S)/(20
R) alcohols up to 35% from 5% in a standard sodium borohydride reduction.</description><subject>Biological and medical sciences</subject><subject>Borohydride reduction</subject><subject>Borohydrides - chemistry</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Ketones - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Structure</subject><subject>Oxidation-Reduction</subject><subject>Stereoisomerism</subject><subject>Stereoselectivity</subject><subject>Steroid</subject><subject>Steroids - chemistry</subject><subject>Synthesis</subject><subject>Vertebrates: endocrinology</subject><issn>0039-128X</issn><issn>1878-5867</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkUtP3DAUhS1UBFPgL6BsUFeZ-kXi7KgQfUgjdUErdWf5cVM8zcTU10Gd_nqczgDdsTrS9XeOr48JOWd0yShr3q-XmCHF4HHJaRlSuSxyQBZMtaq-VE37hiwoFV3NuPpxTN4irimljej4ETnmVLZUMbkgf25LDESEAVwODyFvq9hXGH2YNpWNKd5tfQoeqgR-KkQc_52bPCWTwVf7LcxQ_YIcR8BqymEIf8P4s3Jx9GG24OxZTe7uv5hTctibAeFsryfk-8ebb9ef69XXT1-uP6xqJ7o2153tADiH8hQKfWulYo111gkuXKOM5E5IbtWlospTZkE2lnnGyrBvpbQgTsi7Xe59ir8nwKw3AR0MgxkhTqhbITpVDLyQzY50KSIm6PV9ChuTtppRPZeu1_qpdD2XrqnURYrxfH_FZDfgn21PLRfgYg8YdGbokxldwBeOdx0VauaudhyUQh4CJI0uwOjAh1S-R_sYXtvlEaSepxU</recordid><startdate>20101001</startdate><enddate>20101001</enddate><creator>Šťastná, Eva</creator><creator>Černý, Ivan</creator><creator>Pouzar, Vladimír</creator><creator>Chodounská, Hana</creator><general>Elsevier Inc</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20101001</creationdate><title>Stereoselectivity of sodium borohydride reduction of saturated steroidal ketones utilizing conditions of Luche reduction</title><author>Šťastná, Eva ; Černý, Ivan ; Pouzar, Vladimír ; Chodounská, Hana</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c397t-9b9ee22e0030ef7b4816bcbc323c68a42c342b85808d01be46b1d11342f744be3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Biological and medical sciences</topic><topic>Borohydride reduction</topic><topic>Borohydrides - chemistry</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Ketones - chemistry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Structure</topic><topic>Oxidation-Reduction</topic><topic>Stereoisomerism</topic><topic>Stereoselectivity</topic><topic>Steroid</topic><topic>Steroids - chemistry</topic><topic>Synthesis</topic><topic>Vertebrates: endocrinology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Šťastná, Eva</creatorcontrib><creatorcontrib>Černý, Ivan</creatorcontrib><creatorcontrib>Pouzar, Vladimír</creatorcontrib><creatorcontrib>Chodounská, Hana</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Steroids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Šťastná, Eva</au><au>Černý, Ivan</au><au>Pouzar, Vladimír</au><au>Chodounská, Hana</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereoselectivity of sodium borohydride reduction of saturated steroidal ketones utilizing conditions of Luche reduction</atitle><jtitle>Steroids</jtitle><addtitle>Steroids</addtitle><date>2010-10-01</date><risdate>2010</risdate><volume>75</volume><issue>10</issue><spage>721</spage><epage>725</epage><pages>721-725</pages><issn>0039-128X</issn><eissn>1878-5867</eissn><coden>STEDAM</coden><abstract>A series of keto steroids were reduced with sodium borohydride in the presence of cerium(III) chloride or samarium(III) iodide (Luche reduction). The ratios of axial and equatorial alcohols were determined by HPLC and the results were compared with those obtained by a standard sodium borohydride reduction. The best results were obtained with the 2-keto derivative
1, 7-keto derivatives
5 and
6, and 12-keto derivative
8 where the cerium(III) ion addition resulted in the inversion of the axial/equatorial ratios. The Luche reduction of the 20-keto derivative
11 improved the proportion of the (20
S)-alcohol in a mixture of (20
S)/(20
R) alcohols up to 35% from 5% in a standard sodium borohydride reduction.</abstract><cop>Kidlington</cop><pub>Elsevier Inc</pub><pmid>20470814</pmid><doi>10.1016/j.steroids.2010.04.010</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Biological and medical sciences Borohydride reduction Borohydrides - chemistry Fundamental and applied biological sciences. Psychology Ketones - chemistry Magnetic Resonance Spectroscopy Molecular Structure Oxidation-Reduction Stereoisomerism Stereoselectivity Steroid Steroids - chemistry Synthesis Vertebrates: endocrinology |
| title | Stereoselectivity of sodium borohydride reduction of saturated steroidal ketones utilizing conditions of Luche reduction |
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