Photochemical approach to the synthesis of the pyrrolo[1,4]benzodiazepine antibiotics
The total syntheses of the pyrrolo (1,4)benzodiazepine antitumor antibiotics prothracarcin and DC-81 were realized using, as a key step, the photochemical (2 sigma + 2 pi ) ring expansion of the appropriately substituted N-pentenylphthalimide to afford the corresponding pyrrolobenzazepinedione. Conv...
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| Veröffentlicht in: | Journal of organic chemistry 1989-11, Vol.54 (24), p.5746-5758 |
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| container_end_page | 5758 |
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| container_issue | 24 |
| container_start_page | 5746 |
| container_title | Journal of organic chemistry |
| container_volume | 54 |
| creator | Weidner-Wells, Michele A DeCamp, Ann Mazzocchi, Paul H |
| description | The total syntheses of the pyrrolo (1,4)benzodiazepine antitumor antibiotics prothracarcin and DC-81 were realized using, as a key step, the photochemical (2 sigma + 2 pi ) ring expansion of the appropriately substituted N-pentenylphthalimide to afford the corresponding pyrrolobenzazepinedione. Conversion of the photoproduct into the antibiotic skeleton was effected by transformation of the benzylic ketone into a carbinolamine via a Curtius rearrangement sequence. |
| doi_str_mv | 10.1021/jo00285a022 |
| format | Article |
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Org. Chem</addtitle><description>The total syntheses of the pyrrolo (1,4)benzodiazepine antitumor antibiotics prothracarcin and DC-81 were realized using, as a key step, the photochemical (2 sigma + 2 pi ) ring expansion of the appropriately substituted N-pentenylphthalimide to afford the corresponding pyrrolobenzazepinedione. Conversion of the photoproduct into the antibiotic skeleton was effected by transformation of the benzylic ketone into a carbinolamine via a Curtius rearrangement sequence.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1989</creationdate><recordtype>article</recordtype><recordid>eNptkE1LAzEQhoMoWKsn_8AeRA-6mo9Nmj1K8QuKCm1BFAmz2SxN3W7WZAvWX2-0RTw4l4F3nnlneBE6JPicYEou5g5jKjlgSrdQj3CKU5HjbBv1ok5TRgXbRXshzHEsznkPTR9nrnN6ZhZWQ51A23oHepZ0LulmJgmrJrZgQ-KqH6Fdee9q90LOstfCNJ-utPBpWtuYBJrOFtZ1Vod9tFNBHczBpvfR9PpqMrxNRw83d8PLUQpMkC4FXLEqx0B4KQ1kJRdMaplJIgvJdVnIqihJloPMDNPAJRdZSbkWuSwYzrBmfXS89o1fvy9N6NTCBm3qGhrjlkERLnLKyCCCp2tQexeCN5VqvV2AXymC1Xd06k90kT7a2EKIqVQeGm3D74oQciCIiFi6xmzozMfvGPybEgM24GryOFbPcvwk8uG9Gkb-ZM2DDvHe0jcxm38f-ALcTopP</recordid><startdate>19891101</startdate><enddate>19891101</enddate><creator>Weidner-Wells, Michele A</creator><creator>DeCamp, Ann</creator><creator>Mazzocchi, Paul H</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>19891101</creationdate><title>Photochemical approach to the synthesis of the pyrrolo[1,4]benzodiazepine antibiotics</title><author>Weidner-Wells, Michele A ; DeCamp, Ann ; Mazzocchi, Paul H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a361t-a0f3f90a15d8ea4d5638c84818b85cdb8fbd149a84e3ca58564d25c698b3040c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1989</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Weidner-Wells, Michele A</creatorcontrib><creatorcontrib>DeCamp, Ann</creatorcontrib><creatorcontrib>Mazzocchi, Paul H</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Weidner-Wells, Michele A</au><au>DeCamp, Ann</au><au>Mazzocchi, Paul H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photochemical approach to the synthesis of the pyrrolo[1,4]benzodiazepine antibiotics</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. 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| ispartof | Journal of organic chemistry, 1989-11, Vol.54 (24), p.5746-5758 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_15692317 |
| source | ACS Publications |
| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties |
| title | Photochemical approach to the synthesis of the pyrrolo[1,4]benzodiazepine antibiotics |
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