A Versatile Approach for Synthesis of 2,3-Dimethyl Chroman-4-ones, Intermediate for Calanolide Anti-HIV Agents, VIA Aldol/Mitsunobu Reactions
Combined aldol/Mitsunobu reactions have been employed for the first time for synthesis of 2,3-dimethyl chroman-4-ones, intermediates for calanolide anti-HIV agents. Thus, the lithium enolate of chromene 1 reacted with acetaldehyde at -78°C to afford the aldol products 4 and 5. Under Mitsunobu condit...
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| Veröffentlicht in: | Synthetic communications 1996-10, Vol.26 (20), p.3757-3771 |
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| container_title | Synthetic communications |
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| creator | Khilevich, Albert Rizzo, John D. Flavin, Michael T. Sheinkman, Abram K. Mar, Aye Kucherenko, Alla Yan, Changren Dzekhtser, Sergey Brankovic, Darko Lin, Lin Liu, Jinjun Rizzo, Thomas M. Xu, Ze-Qi |
| description | Combined aldol/Mitsunobu reactions have been employed for the first time for synthesis of 2,3-dimethyl chroman-4-ones, intermediates for calanolide anti-HIV agents. Thus, the lithium enolate of chromene 1 reacted with acetaldehyde at -78°C to afford the aldol products 4 and 5. Under Mitsunobu conditions (Ph
3
P/DEAD), the syn aldol product 4 led to the formation of trans-2,3-dimethyl chroman-4-one 2 while the anti aldol product 5 yielded both trans and cis derivatives (2 and 3). The use of other phosphorous and azo compounds in this reaction has also been investigated. |
| doi_str_mv | 10.1080/00397919608003792 |
| format | Article |
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3
P/DEAD), the syn aldol product 4 led to the formation of trans-2,3-dimethyl chroman-4-one 2 while the anti aldol product 5 yielded both trans and cis derivatives (2 and 3). The use of other phosphorous and azo compounds in this reaction has also been investigated.</description><identifier>ISSN: 0039-7911</identifier><identifier>EISSN: 1532-2432</identifier><identifier>DOI: 10.1080/00397919608003792</identifier><language>eng</language><publisher>Taylor & Francis Group</publisher><ispartof>Synthetic communications, 1996-10, Vol.26 (20), p.3757-3771</ispartof><rights>Copyright Taylor & Francis Group, LLC 1996</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c296t-51e4a787a7886f0086b84e0d2e90065ff364d6dcea799070bdd7c2f38c18d9083</citedby><cites>FETCH-LOGICAL-c296t-51e4a787a7886f0086b84e0d2e90065ff364d6dcea799070bdd7c2f38c18d9083</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.tandfonline.com/doi/pdf/10.1080/00397919608003792$$EPDF$$P50$$Ginformaworld$$H</linktopdf><linktohtml>$$Uhttps://www.tandfonline.com/doi/full/10.1080/00397919608003792$$EHTML$$P50$$Ginformaworld$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,59620,60409</link.rule.ids></links><search><creatorcontrib>Khilevich, Albert</creatorcontrib><creatorcontrib>Rizzo, John D.</creatorcontrib><creatorcontrib>Flavin, Michael T.</creatorcontrib><creatorcontrib>Sheinkman, Abram K.</creatorcontrib><creatorcontrib>Mar, Aye</creatorcontrib><creatorcontrib>Kucherenko, Alla</creatorcontrib><creatorcontrib>Yan, Changren</creatorcontrib><creatorcontrib>Dzekhtser, Sergey</creatorcontrib><creatorcontrib>Brankovic, Darko</creatorcontrib><creatorcontrib>Lin, Lin</creatorcontrib><creatorcontrib>Liu, Jinjun</creatorcontrib><creatorcontrib>Rizzo, Thomas M.</creatorcontrib><creatorcontrib>Xu, Ze-Qi</creatorcontrib><title>A Versatile Approach for Synthesis of 2,3-Dimethyl Chroman-4-ones, Intermediate for Calanolide Anti-HIV Agents, VIA Aldol/Mitsunobu Reactions</title><title>Synthetic communications</title><description>Combined aldol/Mitsunobu reactions have been employed for the first time for synthesis of 2,3-dimethyl chroman-4-ones, intermediates for calanolide anti-HIV agents. Thus, the lithium enolate of chromene 1 reacted with acetaldehyde at -78°C to afford the aldol products 4 and 5. Under Mitsunobu conditions (Ph
3
P/DEAD), the syn aldol product 4 led to the formation of trans-2,3-dimethyl chroman-4-one 2 while the anti aldol product 5 yielded both trans and cis derivatives (2 and 3). The use of other phosphorous and azo compounds in this reaction has also been investigated.</description><issn>0039-7911</issn><issn>1532-2432</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1996</creationdate><recordtype>article</recordtype><recordid>eNp1kN1KAzEQhYMoWKsP4F0ewOhks91NwJul_rSgCP70dkk3iY1kk5JEZB_Cd3a13okXwzDM-Q6cg9AphXMKHC4AmKgFFdV4AKtFsYcmdMYKUpSs2EeT7z8ZBfQQHaX0BkBnNRcT9NnglY5JZus0brbbGGS3wSZE_DT4vNHJJhwMLs4YubK9zpvB4fkmhl56UpLgdTrDS5917LWyMusfdC6d9MFZNVr6bMliucLNq_Z5FK-WDW6cCu7i3ub07sP6HT9q2WUbfDpGB0a6pE9-9xS93Fw_zxfk7uF2OW_uSFeIKpMZ1aWseT0OrwwAr9a81KAKLQCqmTGsKlWlOi1rIaCGtVJ1VxjGO8qVAM6miO58uxhSitq022h7GYeWQvvdZ_unz5G53DHWjxl7-RGiU22WgwvRROk7m1r2P_4Fjpt63g</recordid><startdate>19961001</startdate><enddate>19961001</enddate><creator>Khilevich, Albert</creator><creator>Rizzo, John D.</creator><creator>Flavin, Michael T.</creator><creator>Sheinkman, Abram K.</creator><creator>Mar, Aye</creator><creator>Kucherenko, Alla</creator><creator>Yan, Changren</creator><creator>Dzekhtser, Sergey</creator><creator>Brankovic, Darko</creator><creator>Lin, Lin</creator><creator>Liu, Jinjun</creator><creator>Rizzo, Thomas M.</creator><creator>Xu, Ze-Qi</creator><general>Taylor & Francis Group</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19961001</creationdate><title>A Versatile Approach for Synthesis of 2,3-Dimethyl Chroman-4-ones, Intermediate for Calanolide Anti-HIV Agents, VIA Aldol/Mitsunobu Reactions</title><author>Khilevich, Albert ; Rizzo, John D. ; Flavin, Michael T. ; Sheinkman, Abram K. ; Mar, Aye ; Kucherenko, Alla ; Yan, Changren ; Dzekhtser, Sergey ; Brankovic, Darko ; Lin, Lin ; Liu, Jinjun ; Rizzo, Thomas M. ; Xu, Ze-Qi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c296t-51e4a787a7886f0086b84e0d2e90065ff364d6dcea799070bdd7c2f38c18d9083</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1996</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Khilevich, Albert</creatorcontrib><creatorcontrib>Rizzo, John D.</creatorcontrib><creatorcontrib>Flavin, Michael T.</creatorcontrib><creatorcontrib>Sheinkman, Abram K.</creatorcontrib><creatorcontrib>Mar, Aye</creatorcontrib><creatorcontrib>Kucherenko, Alla</creatorcontrib><creatorcontrib>Yan, Changren</creatorcontrib><creatorcontrib>Dzekhtser, Sergey</creatorcontrib><creatorcontrib>Brankovic, Darko</creatorcontrib><creatorcontrib>Lin, Lin</creatorcontrib><creatorcontrib>Liu, Jinjun</creatorcontrib><creatorcontrib>Rizzo, Thomas M.</creatorcontrib><creatorcontrib>Xu, Ze-Qi</creatorcontrib><collection>CrossRef</collection><jtitle>Synthetic communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Khilevich, Albert</au><au>Rizzo, John D.</au><au>Flavin, Michael T.</au><au>Sheinkman, Abram K.</au><au>Mar, Aye</au><au>Kucherenko, Alla</au><au>Yan, Changren</au><au>Dzekhtser, Sergey</au><au>Brankovic, Darko</au><au>Lin, Lin</au><au>Liu, Jinjun</au><au>Rizzo, Thomas M.</au><au>Xu, Ze-Qi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Versatile Approach for Synthesis of 2,3-Dimethyl Chroman-4-ones, Intermediate for Calanolide Anti-HIV Agents, VIA Aldol/Mitsunobu Reactions</atitle><jtitle>Synthetic communications</jtitle><date>1996-10-01</date><risdate>1996</risdate><volume>26</volume><issue>20</issue><spage>3757</spage><epage>3771</epage><pages>3757-3771</pages><issn>0039-7911</issn><eissn>1532-2432</eissn><abstract>Combined aldol/Mitsunobu reactions have been employed for the first time for synthesis of 2,3-dimethyl chroman-4-ones, intermediates for calanolide anti-HIV agents. Thus, the lithium enolate of chromene 1 reacted with acetaldehyde at -78°C to afford the aldol products 4 and 5. Under Mitsunobu conditions (Ph
3
P/DEAD), the syn aldol product 4 led to the formation of trans-2,3-dimethyl chroman-4-one 2 while the anti aldol product 5 yielded both trans and cis derivatives (2 and 3). The use of other phosphorous and azo compounds in this reaction has also been investigated.</abstract><pub>Taylor & Francis Group</pub><doi>10.1080/00397919608003792</doi><tpages>15</tpages></addata></record> |
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| source | Taylor & Francis Journals Complete |
| title | A Versatile Approach for Synthesis of 2,3-Dimethyl Chroman-4-ones, Intermediate for Calanolide Anti-HIV Agents, VIA Aldol/Mitsunobu Reactions |
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