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Studies of the synthesis of 5-hydroxy 6-keto steroids and related 6-keto steroids
Syntheses of 5-hydroxy-5α- and 5β-cholestan-6-one (11 and 13 ) and their 3β-acetoxy ( 10 and 21 ) and 3β-benzyloxy derivatives ( 12 and 19 ) are described, as are syntheses of the 7α-deutero derivatives of 10 and 21 . Related investigations of the syntheses of the 5-methoxy and 5-methyl analogues of...
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| Published in: | Canadian journal of chemistry 1987-09, Vol.65 (9), p.2203-2216 |
|---|---|
| Main Authors: | , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c384t-3bc975499da08b2785ed846c7998dda89976758851f49d20ba8de8c74c8a8c203 |
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| container_end_page | 2216 |
| container_issue | 9 |
| container_start_page | 2203 |
| container_title | Canadian journal of chemistry |
| container_volume | 65 |
| creator | Yates, Peter Stiver, Shirley |
| description | Syntheses of 5-hydroxy-5α- and 5β-cholestan-6-one
(11
and
13
) and their 3β-acetoxy (
10
and
21
) and 3β-benzyloxy derivatives (
12
and
19
) are described, as are syntheses of the 7α-deutero derivatives of
10
and
21
. Related investigations of the syntheses of the 5-methoxy and 5-methyl analogues of these compounds are also discussed. Treatment of
12
with potassium tert-butoxide has been shown to give 5-hydroxy-5β-cholest-3-en-6-one (
14
) and its Δ
2
isomer
15
. Reaction of 6-nitrocholesteryl acetate (
50
) with lithium dimethylcuprate gives 3α,5-cyclo-5α-cholestan-6-one (E)-oxime (
51
) as the major product. |
| doi_str_mv | 10.1139/v87-369 |
| format | article |
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(11
and
13
) and their 3β-acetoxy (
10
and
21
) and 3β-benzyloxy derivatives (
12
and
19
) are described, as are syntheses of the 7α-deutero derivatives of
10
and
21
. Related investigations of the syntheses of the 5-methoxy and 5-methyl analogues of these compounds are also discussed. Treatment of
12
with potassium tert-butoxide has been shown to give 5-hydroxy-5β-cholest-3-en-6-one (
14
) and its Δ
2
isomer
15
. Reaction of 6-nitrocholesteryl acetate (
50
) with lithium dimethylcuprate gives 3α,5-cyclo-5α-cholestan-6-one (E)-oxime (
51
) as the major product.</description><identifier>ISSN: 0008-4042</identifier><identifier>EISSN: 1480-3291</identifier><identifier>DOI: 10.1139/v87-369</identifier><identifier>CODEN: CJCHAG</identifier><language>eng</language><publisher>Ottawa, Canada: NRC Research Press</publisher><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids ; Chemistry ; Exact sciences and technology ; Organic chemistry ; Preparations and properties ; Steroids</subject><ispartof>Canadian journal of chemistry, 1987-09, Vol.65 (9), p.2203-2216</ispartof><rights>1988 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c384t-3bc975499da08b2785ed846c7998dda89976758851f49d20ba8de8c74c8a8c203</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=7616689$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Yates, Peter</creatorcontrib><creatorcontrib>Stiver, Shirley</creatorcontrib><title>Studies of the synthesis of 5-hydroxy 6-keto steroids and related 6-keto steroids</title><title>Canadian journal of chemistry</title><addtitle>Revue canadienne de chimie</addtitle><description>Syntheses of 5-hydroxy-5α- and 5β-cholestan-6-one
(11
and
13
) and their 3β-acetoxy (
10
and
21
) and 3β-benzyloxy derivatives (
12
and
19
) are described, as are syntheses of the 7α-deutero derivatives of
10
and
21
. Related investigations of the syntheses of the 5-methoxy and 5-methyl analogues of these compounds are also discussed. Treatment of
12
with potassium tert-butoxide has been shown to give 5-hydroxy-5β-cholest-3-en-6-one (
14
) and its Δ
2
isomer
15
. Reaction of 6-nitrocholesteryl acetate (
50
) with lithium dimethylcuprate gives 3α,5-cyclo-5α-cholestan-6-one (E)-oxime (
51
) as the major product.</description><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Steroids</subject><issn>0008-4042</issn><issn>1480-3291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1987</creationdate><recordtype>article</recordtype><recordid>eNp90E1LxDAQBuAgCq6r-BdyEAUhmjRpMjnKsn7Agoh6LtkkZau1LZkq9t_bdRcPgp5eZuZhDi8hx4JfCCHt5QcYJrXdIROhgDOZWbFLJpxzYIqrbJ8cIL6Mo-FZPiEPj_17qCLStqT9KlIcmjGw-l7kbDWE1H4OVLPX2LcU-5jaKiB1TaAp1q6P4fftkOyVrsZ4tM0peb6eP81u2eL-5m52tWBeguqZXHprcmVtcByWmYE8BlDaG2shBAfWGm1ygFyUyoaMLx2ECN4oDw58xuWUnG3--tQiplgWXareXBoKwYt1E8XYRDE2McqTjewceleXyTW-wh9utNAa1ux8w5rkU8Tokl_98_P0b7xFRRdK-QWrXHiO</recordid><startdate>19870901</startdate><enddate>19870901</enddate><creator>Yates, Peter</creator><creator>Stiver, Shirley</creator><general>NRC Research Press</general><general>National Research Council of Canada</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19870901</creationdate><title>Studies of the synthesis of 5-hydroxy 6-keto steroids and related 6-keto steroids</title><author>Yates, Peter ; Stiver, Shirley</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c384t-3bc975499da08b2785ed846c7998dda89976758851f49d20ba8de8c74c8a8c203</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1987</creationdate><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Steroids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yates, Peter</creatorcontrib><creatorcontrib>Stiver, Shirley</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Canadian journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yates, Peter</au><au>Stiver, Shirley</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Studies of the synthesis of 5-hydroxy 6-keto steroids and related 6-keto steroids</atitle><jtitle>Canadian journal of chemistry</jtitle><addtitle>Revue canadienne de chimie</addtitle><date>1987-09-01</date><risdate>1987</risdate><volume>65</volume><issue>9</issue><spage>2203</spage><epage>2216</epage><pages>2203-2216</pages><issn>0008-4042</issn><eissn>1480-3291</eissn><coden>CJCHAG</coden><abstract>Syntheses of 5-hydroxy-5α- and 5β-cholestan-6-one
(11
and
13
) and their 3β-acetoxy (
10
and
21
) and 3β-benzyloxy derivatives (
12
and
19
) are described, as are syntheses of the 7α-deutero derivatives of
10
and
21
. Related investigations of the syntheses of the 5-methoxy and 5-methyl analogues of these compounds are also discussed. Treatment of
12
with potassium tert-butoxide has been shown to give 5-hydroxy-5β-cholest-3-en-6-one (
14
) and its Δ
2
isomer
15
. Reaction of 6-nitrocholesteryl acetate (
50
) with lithium dimethylcuprate gives 3α,5-cyclo-5α-cholestan-6-one (E)-oxime (
51
) as the major product.</abstract><cop>Ottawa, Canada</cop><pub>NRC Research Press</pub><doi>10.1139/v87-369</doi><tpages>14</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0008-4042 |
| ispartof | Canadian journal of chemistry, 1987-09, Vol.65 (9), p.2203-2216 |
| issn | 0008-4042 1480-3291 |
| language | eng |
| recordid | cdi_pascalfrancis_primary_7616689 |
| source | EZB Electronic Journals Library |
| subjects | Alicyclic compounds, terpenoids, prostaglandins, steroids Chemistry Exact sciences and technology Organic chemistry Preparations and properties Steroids |
| title | Studies of the synthesis of 5-hydroxy 6-keto steroids and related 6-keto steroids |
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