One‐Pot Oxidation of Secondary Alcohols to α‐Hydroxy Ketones: Application to Synthesis of Oxoaplysinopsin D, E, F, & G
A simple one‐pot transformation of secondary alcohols to α‐hydroxy ketones using pyridinium dichromate (PDC) in DMF has been developed and substrate scope tested with 25 compounds of hydantoin derivatives. Using this method, we have devised a common dihydroxy intermediate and synthesized four natura...
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| Veröffentlicht in: | European journal of organic chemistry 2021-04, Vol.2021 (15), p.2188-2192 |
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| container_title | European journal of organic chemistry |
| container_volume | 2021 |
| creator | Kulkarni, Akshay S. Ramesh, Eagala Srinivasa Reddy, D. |
| description | A simple one‐pot transformation of secondary alcohols to α‐hydroxy ketones using pyridinium dichromate (PDC) in DMF has been developed and substrate scope tested with 25 compounds of hydantoin derivatives. Using this method, we have devised a common dihydroxy intermediate and synthesized four natural products oxoaplysinopsins D, E, F, and G for the first time.
A one‐pot method for the transformation of secondary alcohols to α‐hydroxy ketones using pyridinium dichromate (PDC) at room temperature is described. The method was tested with a variety of hydantoin derivatives. As a direct application, total synthesis of four natural oxoaplysinopsins D, E, F and G was accomplished for the first time through a common dihydroxy intermediate. |
| doi_str_mv | 10.1002/ejoc.202100184 |
| format | Article |
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A one‐pot method for the transformation of secondary alcohols to α‐hydroxy ketones using pyridinium dichromate (PDC) at room temperature is described. The method was tested with a variety of hydantoin derivatives. As a direct application, total synthesis of four natural oxoaplysinopsins D, E, F and G was accomplished for the first time through a common dihydroxy intermediate.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202100184</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Alcohols ; Chromates ; Hydantoin ; Ketones ; Natural product ; Natural products ; Oxidation ; Oxoaplysinopsin ; Retro-aldol ; Substrates ; α-Hydroxylation</subject><ispartof>European journal of organic chemistry, 2021-04, Vol.2021 (15), p.2188-2192</ispartof><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2474-2051994d7987bc870ed24fbdce78b927fca4dfc096cd385289e3944ecd7e316b3</citedby><cites>FETCH-LOGICAL-c2474-2051994d7987bc870ed24fbdce78b927fca4dfc096cd385289e3944ecd7e316b3</cites><orcidid>0000-0003-3270-315X</orcidid></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.202100184$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.202100184$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Kulkarni, Akshay S.</creatorcontrib><creatorcontrib>Ramesh, Eagala</creatorcontrib><creatorcontrib>Srinivasa Reddy, D.</creatorcontrib><title>One‐Pot Oxidation of Secondary Alcohols to α‐Hydroxy Ketones: Application to Synthesis of Oxoaplysinopsin D, E, F, & G</title><title>European journal of organic chemistry</title><description>A simple one‐pot transformation of secondary alcohols to α‐hydroxy ketones using pyridinium dichromate (PDC) in DMF has been developed and substrate scope tested with 25 compounds of hydantoin derivatives. Using this method, we have devised a common dihydroxy intermediate and synthesized four natural products oxoaplysinopsins D, E, F, and G for the first time.
A one‐pot method for the transformation of secondary alcohols to α‐hydroxy ketones using pyridinium dichromate (PDC) at room temperature is described. The method was tested with a variety of hydantoin derivatives. As a direct application, total synthesis of four natural oxoaplysinopsins D, E, F and G was accomplished for the first time through a common dihydroxy intermediate.</description><subject>Alcohols</subject><subject>Chromates</subject><subject>Hydantoin</subject><subject>Ketones</subject><subject>Natural product</subject><subject>Natural products</subject><subject>Oxidation</subject><subject>Oxoaplysinopsin</subject><subject>Retro-aldol</subject><subject>Substrates</subject><subject>α-Hydroxylation</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkM1KxDAUhYMoOI5uXQcEV9MxSTNN424Y50cdqDAK7kKbpEyH2tSmgy1ufARfxRfxIXwSM1R06eb-wHfO5R4ATjEaYoTIhd4YOSSIuAWHdA_0MOLcQwFH-26mPvUw9x8PwZG1G4QQDwLcA69Rob_e3u9MDaMmU3GdmQKaFK60NIWKqxaOc2nWJrewNvDzw7GLVlWmaeGtrk2h7SUcl2WeyU7qoFVb1GttM7vziRoTl3lrs8KUrsCrAZwO4GwAz-H8GBykcW71yU_vg4fZ9H6y8JbR_HoyXnqSUEY9gkaYc6oYD1kiQ4a0IjRNlNQsTDhhqYypSqV7SCo_HJGQa59TqqVi2sdB4vfBWedbVuZ5q20tNmZbFe6kICPHY0RZ6KhhR8nKWFvpVJRV9uQSEBiJXcBiF7D4DdgJeCd4yXLd_kOL6U00-dN-AywSga4</recordid><startdate>20210422</startdate><enddate>20210422</enddate><creator>Kulkarni, Akshay S.</creator><creator>Ramesh, Eagala</creator><creator>Srinivasa Reddy, D.</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-3270-315X</orcidid></search><sort><creationdate>20210422</creationdate><title>One‐Pot Oxidation of Secondary Alcohols to α‐Hydroxy Ketones: Application to Synthesis of Oxoaplysinopsin D, E, F, & G</title><author>Kulkarni, Akshay S. ; Ramesh, Eagala ; Srinivasa Reddy, D.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2474-2051994d7987bc870ed24fbdce78b927fca4dfc096cd385289e3944ecd7e316b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Alcohols</topic><topic>Chromates</topic><topic>Hydantoin</topic><topic>Ketones</topic><topic>Natural product</topic><topic>Natural products</topic><topic>Oxidation</topic><topic>Oxoaplysinopsin</topic><topic>Retro-aldol</topic><topic>Substrates</topic><topic>α-Hydroxylation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kulkarni, Akshay S.</creatorcontrib><creatorcontrib>Ramesh, Eagala</creatorcontrib><creatorcontrib>Srinivasa Reddy, D.</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kulkarni, Akshay S.</au><au>Ramesh, Eagala</au><au>Srinivasa Reddy, D.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One‐Pot Oxidation of Secondary Alcohols to α‐Hydroxy Ketones: Application to Synthesis of Oxoaplysinopsin D, E, F, & G</atitle><jtitle>European journal of organic chemistry</jtitle><date>2021-04-22</date><risdate>2021</risdate><volume>2021</volume><issue>15</issue><spage>2188</spage><epage>2192</epage><pages>2188-2192</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>A simple one‐pot transformation of secondary alcohols to α‐hydroxy ketones using pyridinium dichromate (PDC) in DMF has been developed and substrate scope tested with 25 compounds of hydantoin derivatives. Using this method, we have devised a common dihydroxy intermediate and synthesized four natural products oxoaplysinopsins D, E, F, and G for the first time.
A one‐pot method for the transformation of secondary alcohols to α‐hydroxy ketones using pyridinium dichromate (PDC) at room temperature is described. The method was tested with a variety of hydantoin derivatives. As a direct application, total synthesis of four natural oxoaplysinopsins D, E, F and G was accomplished for the first time through a common dihydroxy intermediate.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.202100184</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0003-3270-315X</orcidid></addata></record> |
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| subjects | Alcohols Chromates Hydantoin Ketones Natural product Natural products Oxidation Oxoaplysinopsin Retro-aldol Substrates α-Hydroxylation |
| title | One‐Pot Oxidation of Secondary Alcohols to α‐Hydroxy Ketones: Application to Synthesis of Oxoaplysinopsin D, E, F, & G |
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