Application of Lewis Acid Catalyzed Tropone [6+4] Cycloadditions to the Synthesis of the Core of CP-225,917
The carbocyclic core of CP-225,917 and CP-263,114 is accessible through the [6+4] cycloaddition of a tropone with a 2-substituted cyclopentadiene. Examination of this reaction has revealed for the first time that this cycloaddition process is catalyzed by Lewis acids, including lanthanide triflates....
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| Veröffentlicht in: | Organic letters 2001-12, Vol.3 (26), p.4189-4192 |
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| creator | Isakovic, Ljubomir Ashenhurst, James A Gleason, James L |
| description | The carbocyclic core of CP-225,917 and CP-263,114 is accessible through the [6+4] cycloaddition of a tropone with a 2-substituted cyclopentadiene. Examination of this reaction has revealed for the first time that this cycloaddition process is catalyzed by Lewis acids, including lanthanide triflates. Cycloadditions of several mono-, di-, and trisubstituted tropones with 2-silyloxycyclopentadienes using ZnCl2 catalysis are found to proceed in good yield and, in many cases, with excellent diastereoselectivity. Subsequent transformation to the core of the CP-molecules involves a site-selective Baeyer−Villiger oxidation of a tricyclic diketone, followed by a syn-elimination process. |
| doi_str_mv | 10.1021/ol016814h |
| format | Article |
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Examination of this reaction has revealed for the first time that this cycloaddition process is catalyzed by Lewis acids, including lanthanide triflates. Cycloadditions of several mono-, di-, and trisubstituted tropones with 2-silyloxycyclopentadienes using ZnCl2 catalysis are found to proceed in good yield and, in many cases, with excellent diastereoselectivity. 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Subsequent transformation to the core of the CP-molecules involves a site-selective Baeyer−Villiger oxidation of a tricyclic diketone, followed by a syn-elimination process.</description><subject>Acids - chemistry</subject><subject>Catalysis</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Farnesyl-Diphosphate Farnesyltransferase - antagonists & inhibitors</subject><subject>Maleic Anhydrides - chemical synthesis</subject><subject>Maleic Anhydrides - chemistry</subject><subject>Tropolone - analogs & derivatives</subject><subject>Tropolone - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkF9LwzAUxYMobk4f_AKSFwXRam6bNO3jKP6DgYLzSaRkSco6u6YmLVI_vSkb88Wnezj8zoF7EDoFcgMkhFtTEYgToMs9NAYWRgEnLNzf6ZiM0JFzK0LAO-khGgHwhAKnY_Q5bZqqlKItTY1NgWf6u3R4KkuFM9GKqv_RCs-taUyt8Xt8RT9w1svKCKXKIeNwa3C71Pi1r_1xPuxbBiMzVg86ewnCkF2nwI_RQSEqp0-2d4Le7u_m2WMwe354yqazQEQAbbCgcsFiLphICgVUxmHCU0FSLQhElBUqpizhvFCaA2W0UIKwlC0E8QJkyqIJutj0NtZ8ddq1-bp0UleVqLXpXM7DKGVxGnrwcgNKa5yzusgbW66F7XMg-bBsvlvWs2fb0m6x1uqP3E7pgfMNIKTLV6aztf_xn6Jfkk99WA</recordid><startdate>20011227</startdate><enddate>20011227</enddate><creator>Isakovic, Ljubomir</creator><creator>Ashenhurst, James A</creator><creator>Gleason, James L</creator><general>American Chemical Society</general><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>20011227</creationdate><title>Application of Lewis Acid Catalyzed Tropone [6+4] Cycloadditions to the Synthesis of the Core of CP-225,917</title><author>Isakovic, Ljubomir ; Ashenhurst, James A ; Gleason, James L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a311t-b4cb567a5a8fd14c62879a09ea01345fd645877fde71454fda0595ba0da01c953</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Acids - chemistry</topic><topic>Catalysis</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Farnesyl-Diphosphate Farnesyltransferase - antagonists & inhibitors</topic><topic>Maleic Anhydrides - chemical synthesis</topic><topic>Maleic Anhydrides - chemistry</topic><topic>Tropolone - analogs & derivatives</topic><topic>Tropolone - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Isakovic, Ljubomir</creatorcontrib><creatorcontrib>Ashenhurst, James A</creatorcontrib><creatorcontrib>Gleason, James L</creatorcontrib><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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Isakovic, Ljubomir</au><au>Ashenhurst, James A</au><au>Gleason, James L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Application of Lewis Acid Catalyzed Tropone [6+4] Cycloadditions to the Synthesis of the Core of CP-225,917</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2001-12, Vol.3 (26), p.4189-4192 |
| issn | 1523-7060 1523-7052 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Acids - chemistry Catalysis Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Farnesyl-Diphosphate Farnesyltransferase - antagonists & inhibitors Maleic Anhydrides - chemical synthesis Maleic Anhydrides - chemistry Tropolone - analogs & derivatives Tropolone - chemistry |
| title | Application of Lewis Acid Catalyzed Tropone [6+4] Cycloadditions to the Synthesis of the Core of CP-225,917 |
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