A Common Synthetic Protocol for the Cyclic and Acyclic Core of Migrastatin, Isomigrastatin, and Dorrigocin via a Chiral β-Hydroxy-γ-butyrolactone Intermediate
A facile synthetic route has been developed for the synthesis of the cyclic and acyclic cores of migrastatin, isomigrastatin, and dorrigocin. The common synthetic route goes via a β‐hydroxy‐γ‐butyrolactone intermediate that is obtained by a PdII‐catalysed asymmetric allylic intramolecular cyclizatio...
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| Veröffentlicht in: | European journal of organic chemistry 2014-10, Vol.2014 (29), p.6558-6564 |
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| container_title | European journal of organic chemistry |
| container_volume | 2014 |
| creator | Gade, Narendar Reddy Iqbal, Javed |
| description | A facile synthetic route has been developed for the synthesis of the cyclic and acyclic cores of migrastatin, isomigrastatin, and dorrigocin. The common synthetic route goes via a β‐hydroxy‐γ‐butyrolactone intermediate that is obtained by a PdII‐catalysed asymmetric allylic intramolecular cyclization of 3‐hydroxy‐2‐methylhex‐5‐enoic acid following a protocol developed by White and coworkers.
The synthesis of a key intermediate chiral β‐hydroxy‐γ‐butyrolactone (A) by PdII‐catalysed stereoselective allylic C–H oxidation is reported. A common synthetic route to transform this intermediate into key building blocks for the synthesis of migrastatin family members has been developed. |
| doi_str_mv | 10.1002/ejoc.201402830 |
| format | Article |
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The synthesis of a key intermediate chiral β‐hydroxy‐γ‐butyrolactone (A) by PdII‐catalysed stereoselective allylic C–H oxidation is reported. A common synthetic route to transform this intermediate into key building blocks for the synthesis of migrastatin family members has been developed.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201402830</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>C-H activation ; Lactones ; Metathesis ; Natural products ; Oxidation ; Synthesis design</subject><ispartof>European journal of organic chemistry, 2014-10, Vol.2014 (29), p.6558-6564</ispartof><rights>Copyright © 2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5370-467e55d7ec6de039ac89d19278fc22fb3bccb30fdb557d941bc72e57409085c83</citedby><cites>FETCH-LOGICAL-c5370-467e55d7ec6de039ac89d19278fc22fb3bccb30fdb557d941bc72e57409085c83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.201402830$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201402830$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Gade, Narendar Reddy</creatorcontrib><creatorcontrib>Iqbal, Javed</creatorcontrib><title>A Common Synthetic Protocol for the Cyclic and Acyclic Core of Migrastatin, Isomigrastatin, and Dorrigocin via a Chiral β-Hydroxy-γ-butyrolactone Intermediate</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>A facile synthetic route has been developed for the synthesis of the cyclic and acyclic cores of migrastatin, isomigrastatin, and dorrigocin. The common synthetic route goes via a β‐hydroxy‐γ‐butyrolactone intermediate that is obtained by a PdII‐catalysed asymmetric allylic intramolecular cyclization of 3‐hydroxy‐2‐methylhex‐5‐enoic acid following a protocol developed by White and coworkers.
The synthesis of a key intermediate chiral β‐hydroxy‐γ‐butyrolactone (A) by PdII‐catalysed stereoselective allylic C–H oxidation is reported. A common synthetic route to transform this intermediate into key building blocks for the synthesis of migrastatin family members has been developed.</description><subject>C-H activation</subject><subject>Lactones</subject><subject>Metathesis</subject><subject>Natural products</subject><subject>Oxidation</subject><subject>Synthesis design</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqFkEtOwzAQhiMEElDYsvYBcBnHSRwvqwB9CGgRIBAby3GcYkhi5JhHbsMZ4B49E62KEDtW88-v-WbxBcEBgT4BCI_0o1X9EEgEYUphI9ghwDmGhMPmMkc0woTTu-1gt20fAYAnCdkJPgYos3VtG3TVNf5Be6PQzFlvla1QaR1adijrVLXsZVOggVrnzDqNbInOzdzJ1ktvmkM0bm39d18Bx9Y5M7fKNOjVSCRR9mCcrNDiE4-6wtn3Di--cP7iO2crqbxtNBo3XrtaF0Z6vRdslbJq9f7P7AU3pyfX2QifTYfjbHCGVUwZ4ChhOo4LplVSaKBcqpQXhIcsLVUYljnNlcoplEUex6zgEckVC3XMIuCQxiqlvaC__qucbVunS_HsTC1dJwiIlV-x8it-_S4BvgbeTKW7f67FyWSa_WXxmjWt1--_rHRPImGUxeL2YiiOk9Ht_YRfihn9BqdTkxk</recordid><startdate>201410</startdate><enddate>201410</enddate><creator>Gade, Narendar Reddy</creator><creator>Iqbal, Javed</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201410</creationdate><title>A Common Synthetic Protocol for the Cyclic and Acyclic Core of Migrastatin, Isomigrastatin, and Dorrigocin via a Chiral β-Hydroxy-γ-butyrolactone Intermediate</title><author>Gade, Narendar Reddy ; Iqbal, Javed</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5370-467e55d7ec6de039ac89d19278fc22fb3bccb30fdb557d941bc72e57409085c83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>C-H activation</topic><topic>Lactones</topic><topic>Metathesis</topic><topic>Natural products</topic><topic>Oxidation</topic><topic>Synthesis design</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gade, Narendar Reddy</creatorcontrib><creatorcontrib>Iqbal, Javed</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gade, Narendar Reddy</au><au>Iqbal, Javed</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Common Synthetic Protocol for the Cyclic and Acyclic Core of Migrastatin, Isomigrastatin, and Dorrigocin via a Chiral β-Hydroxy-γ-butyrolactone Intermediate</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2014-10</date><risdate>2014</risdate><volume>2014</volume><issue>29</issue><spage>6558</spage><epage>6564</epage><pages>6558-6564</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>A facile synthetic route has been developed for the synthesis of the cyclic and acyclic cores of migrastatin, isomigrastatin, and dorrigocin. The common synthetic route goes via a β‐hydroxy‐γ‐butyrolactone intermediate that is obtained by a PdII‐catalysed asymmetric allylic intramolecular cyclization of 3‐hydroxy‐2‐methylhex‐5‐enoic acid following a protocol developed by White and coworkers.
The synthesis of a key intermediate chiral β‐hydroxy‐γ‐butyrolactone (A) by PdII‐catalysed stereoselective allylic C–H oxidation is reported. A common synthetic route to transform this intermediate into key building blocks for the synthesis of migrastatin family members has been developed.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201402830</doi><tpages>7</tpages></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | C-H activation Lactones Metathesis Natural products Oxidation Synthesis design |
| title | A Common Synthetic Protocol for the Cyclic and Acyclic Core of Migrastatin, Isomigrastatin, and Dorrigocin via a Chiral β-Hydroxy-γ-butyrolactone Intermediate |
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