Enantioselective synthesis of A 3′-dephenylcryptophycin synthon
An enantioselective synthesis of tert-butyl (5 S,6 R)-( E)-5- tert-butyldimethylsilyloxy-6-methyl-2,7-octadienoate, a precursor for the synthesis of the antimitotic macrolides cryptophycin A and arenastatin A (cryptophycin-24), is presented. The key step in the reaction sequence features a crotyl bo...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 1998-11, Vol.8 (22), p.3177-3180 |
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| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 8 |
| creator | Eggen, MariJean Georg, Gunda I. |
| description | An enantioselective synthesis of
tert-butyl (5
S,6
R)-(
E)-5-
tert-butyldimethylsilyloxy-6-methyl-2,7-octadienoate, a precursor for the synthesis of the antimitotic macrolides cryptophycin A and arenastatin A (cryptophycin-24), is presented. The key step in the reaction sequence features a crotyl boration that sets both stereocenters that become the C16 hydroxyl and C1′ methyl in the cryptophycins. Homologation of the terminal olefin via a Heck reaction is presented.
An enantioselective synthesis of a cryptophycin-1 precursor is presented. The key step in the reaction sequence features a crotyl boration, setting the chiral centers at C1′ and C16. |
| doi_str_mv | 10.1016/S0960-894X(98)00557-5 |
| format | Article |
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tert-butyl (5
S,6
R)-(
E)-5-
tert-butyldimethylsilyloxy-6-methyl-2,7-octadienoate, a precursor for the synthesis of the antimitotic macrolides cryptophycin A and arenastatin A (cryptophycin-24), is presented. The key step in the reaction sequence features a crotyl boration that sets both stereocenters that become the C16 hydroxyl and C1′ methyl in the cryptophycins. Homologation of the terminal olefin via a Heck reaction is presented.
An enantioselective synthesis of a cryptophycin-1 precursor is presented. The key step in the reaction sequence features a crotyl boration, setting the chiral centers at C1′ and C16.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/S0960-894X(98)00557-5</identifier><identifier>PMID: 9873698</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Aliphatic compounds ; Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Biological and medical sciences ; Chemistry ; Depsipeptides ; Exact sciences and technology ; General aspects ; Medical sciences ; Organic chemistry ; Peptides, Cyclic - chemical synthesis ; Peptides, Cyclic - pharmacology ; Pharmacology. Drug treatments ; Preparations and properties ; Stereoisomerism ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 1998-11, Vol.8 (22), p.3177-3180</ispartof><rights>1998</rights><rights>1999 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c389t-bb910d54c3a26387f0390477b44c53839f031ec0f168f5f5559b0250e42336ee3</citedby><cites>FETCH-LOGICAL-c389t-bb910d54c3a26387f0390477b44c53839f031ec0f168f5f5559b0250e42336ee3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S0960-894X(98)00557-5$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27926,27927,45997</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1633824$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9873698$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Eggen, MariJean</creatorcontrib><creatorcontrib>Georg, Gunda I.</creatorcontrib><title>Enantioselective synthesis of A 3′-dephenylcryptophycin synthon</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>An enantioselective synthesis of
tert-butyl (5
S,6
R)-(
E)-5-
tert-butyldimethylsilyloxy-6-methyl-2,7-octadienoate, a precursor for the synthesis of the antimitotic macrolides cryptophycin A and arenastatin A (cryptophycin-24), is presented. The key step in the reaction sequence features a crotyl boration that sets both stereocenters that become the C16 hydroxyl and C1′ methyl in the cryptophycins. Homologation of the terminal olefin via a Heck reaction is presented.
An enantioselective synthesis of a cryptophycin-1 precursor is presented. The key step in the reaction sequence features a crotyl boration, setting the chiral centers at C1′ and C16.</description><subject>Aliphatic compounds</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Biological and medical sciences</subject><subject>Chemistry</subject><subject>Depsipeptides</subject><subject>Exact sciences and technology</subject><subject>General aspects</subject><subject>Medical sciences</subject><subject>Organic chemistry</subject><subject>Peptides, Cyclic - chemical synthesis</subject><subject>Peptides, Cyclic - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1998</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkM1KxDAQx4Mouq4-grAHET1UJ81Hk5Ms4hcIHlTwFtp0yka6aU26Qm8-k4_kk9j9QI-eBmZ-_5nhR8gRhXMKVF48gZaQKM1fT7U6AxAiS8QWGVEuecI4iG0y-kX2yH6MbwCUA-e7ZFerjEmtRmR67XPfuSZijbZzHziJve9mGF2cNNVkOmHfn19Jie0MfV_b0Ldd08566_wabPwB2anyOuLhpo7Jy83189Vd8vB4e381fUgsU7pLikJTKAW3LE8lU1kFTAPPsoJzK5hiemhQtFBRqSpRCSF0AakA5CljEpGNycl6bxua9wXGzsxdtFjXucdmEY3UNKUw0GMi1qANTYwBK9MGN89DbyiYpTqzUmeWXoxWZqXOiCF3tDmwKOZY_qY2rob58WaeR5vXVci9dfFvuWRMpXzALtcYDjI-HAYTrUNvsXRhUGzKxv3zyA9NlYt9</recordid><startdate>19981117</startdate><enddate>19981117</enddate><creator>Eggen, MariJean</creator><creator>Georg, Gunda I.</creator><general>Elsevier Ltd</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>19981117</creationdate><title>Enantioselective synthesis of A 3′-dephenylcryptophycin synthon</title><author>Eggen, MariJean ; Georg, Gunda I.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c389t-bb910d54c3a26387f0390477b44c53839f031ec0f168f5f5559b0250e42336ee3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1998</creationdate><topic>Aliphatic compounds</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Biological and medical sciences</topic><topic>Chemistry</topic><topic>Depsipeptides</topic><topic>Exact sciences and technology</topic><topic>General aspects</topic><topic>Medical sciences</topic><topic>Organic chemistry</topic><topic>Peptides, Cyclic - chemical synthesis</topic><topic>Peptides, Cyclic - pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Eggen, MariJean</creatorcontrib><creatorcontrib>Georg, Gunda I.</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>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Eggen, MariJean</au><au>Georg, Gunda I.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective synthesis of A 3′-dephenylcryptophycin synthon</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>1998-11-17</date><risdate>1998</risdate><volume>8</volume><issue>22</issue><spage>3177</spage><epage>3180</epage><pages>3177-3180</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>An enantioselective synthesis of
tert-butyl (5
S,6
R)-(
E)-5-
tert-butyldimethylsilyloxy-6-methyl-2,7-octadienoate, a precursor for the synthesis of the antimitotic macrolides cryptophycin A and arenastatin A (cryptophycin-24), is presented. The key step in the reaction sequence features a crotyl boration that sets both stereocenters that become the C16 hydroxyl and C1′ methyl in the cryptophycins. Homologation of the terminal olefin via a Heck reaction is presented.
An enantioselective synthesis of a cryptophycin-1 precursor is presented. The key step in the reaction sequence features a crotyl boration, setting the chiral centers at C1′ and C16.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>9873698</pmid><doi>10.1016/S0960-894X(98)00557-5</doi><tpages>4</tpages></addata></record> |
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| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 1998-11, Vol.8 (22), p.3177-3180 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_69121042 |
| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Aliphatic compounds Antineoplastic agents Antineoplastic Agents - chemical synthesis Biological and medical sciences Chemistry Depsipeptides Exact sciences and technology General aspects Medical sciences Organic chemistry Peptides, Cyclic - chemical synthesis Peptides, Cyclic - pharmacology Pharmacology. Drug treatments Preparations and properties Stereoisomerism Structure-Activity Relationship |
| title | Enantioselective synthesis of A 3′-dephenylcryptophycin synthon |
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