Intramolecular Cyclization During Bromination of the Quinoline Alkaloid Haplophyllidine
Bromination of the furanoquinoline alkaloid haplophyllidine by molecular bromine and N -bromosuccinimide was accompanied by intramolecular cyclization to form mixtures of new compounds containing additional penta-, hexa-, and spirocyclic rings incorporating the prenyl group of haplophyllidine. The s...
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| Veröffentlicht in: | Chemistry of natural compounds 2022-11, Vol.58 (6), p.1101-1107 |
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| container_title | Chemistry of natural compounds |
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| creator | Ubaidullaev, A. U. Vinogradova, V. I. Zhurakulov, Sh. N. Mukarramov, N. I. Bobakulov, Kh. M. Turgunov, K. A. Tashkhodzhaev, B. |
| description | Bromination of the furanoquinoline alkaloid haplophyllidine by molecular bromine and
N
-bromosuccinimide was accompanied by intramolecular cyclization to form mixtures of new compounds containing additional penta-, hexa-, and spirocyclic rings incorporating the prenyl group of haplophyllidine. The structures and absolute configurations of the chiral centers of all four bromo-derivatives were elucidated using a combination of NMR spectroscopic methods and X-ray crystal structure analyses. |
| doi_str_mv | 10.1007/s10600-022-03877-6 |
| format | Article |
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N
-bromosuccinimide was accompanied by intramolecular cyclization to form mixtures of new compounds containing additional penta-, hexa-, and spirocyclic rings incorporating the prenyl group of haplophyllidine. The structures and absolute configurations of the chiral centers of all four bromo-derivatives were elucidated using a combination of NMR spectroscopic methods and X-ray crystal structure analyses.</description><identifier>ISSN: 0009-3130</identifier><identifier>EISSN: 1573-8388</identifier><identifier>DOI: 10.1007/s10600-022-03877-6</identifier><identifier>PMID: 36406158</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Alkaloids ; Bromination ; Bromine ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Crystal structure ; NMR ; Nuclear magnetic resonance ; Organic Chemistry ; Plant Sciences ; Quinoline</subject><ispartof>Chemistry of natural compounds, 2022-11, Vol.58 (6), p.1101-1107</ispartof><rights>Springer Science+Business Media, LLC, part of Springer Nature 2022. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.</rights><rights>Springer Science+Business Media, LLC, part of Springer Nature 2022, Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.</rights><rights>COPYRIGHT 2022 Springer</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c575t-8c5b9e92c02bc8f20217bd9ae309cf2b00ea9e6f55580198e4fcd6ede22b9ec33</citedby><cites>FETCH-LOGICAL-c575t-8c5b9e92c02bc8f20217bd9ae309cf2b00ea9e6f55580198e4fcd6ede22b9ec33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s10600-022-03877-6$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s10600-022-03877-6$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>230,314,776,780,881,27901,27902,41464,42533,51294</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36406158$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ubaidullaev, A. U.</creatorcontrib><creatorcontrib>Vinogradova, V. I.</creatorcontrib><creatorcontrib>Zhurakulov, Sh. N.</creatorcontrib><creatorcontrib>Mukarramov, N. I.</creatorcontrib><creatorcontrib>Bobakulov, Kh. M.</creatorcontrib><creatorcontrib>Turgunov, K. A.</creatorcontrib><creatorcontrib>Tashkhodzhaev, B.</creatorcontrib><title>Intramolecular Cyclization During Bromination of the Quinoline Alkaloid Haplophyllidine</title><title>Chemistry of natural compounds</title><addtitle>Chem Nat Compd</addtitle><addtitle>Chem Nat Compd</addtitle><description>Bromination of the furanoquinoline alkaloid haplophyllidine by molecular bromine and
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-bromosuccinimide was accompanied by intramolecular cyclization to form mixtures of new compounds containing additional penta-, hexa-, and spirocyclic rings incorporating the prenyl group of haplophyllidine. The structures and absolute configurations of the chiral centers of all four bromo-derivatives were elucidated using a combination of NMR spectroscopic methods and X-ray crystal structure analyses.</description><subject>Alkaloids</subject><subject>Bromination</subject><subject>Bromine</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Crystal structure</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic Chemistry</subject><subject>Plant Sciences</subject><subject>Quinoline</subject><issn>0009-3130</issn><issn>1573-8388</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp9kk2P0zAQhiMEYsvCH-CAInGBQ5axncTOBamUj620EuJLHC3XmbReHLvYCaL8ehyy7FKEkA-Wx8_7jmb0ZtlDAmcEgD-LBGqAAigtgAnOi_pWtiAVZ4VgQtzOFgDQFIwwOMnuxXiZnqKuxd3shNUl1KQSi-zz2g1B9d6iHq0K-eqgrfmhBuNd_nIMxm3zF8H3xs0l3-XDDvN3o3HeGof50n5R1ps2P1d76_e7g7WmTR_3szudshEfXN2n2afXrz6uzouLt2_Wq-VFoSteDYXQ1abBhmqgGy06CpTwTdsoZNDojm4AUDVYd1VVCSCNwLLTbY0tUpp0mrHT7Pnsux83PbYap3Gs3AfTq3CQXhl5_OPMTm79N9nUaQdlmQyeXBkE_3XEOMjeRI3WKod-jJJyJsoEi6nX47_QSz8Gl8abKM5ZVXJyQ22VRWlc51NfPZnKJaccRFUSmqizf1DptNgb7R12JtWPBE-PBIkZ8PuwVWOMcv3h_TFLZ1YHH2PA7nofBOQUHTlHR6boyF_RkXUSPfpzk9eS31lJAJuBuJ9ygeFm_P_Y_gRfgM6P</recordid><startdate>20221101</startdate><enddate>20221101</enddate><creator>Ubaidullaev, A. U.</creator><creator>Vinogradova, V. I.</creator><creator>Zhurakulov, Sh. N.</creator><creator>Mukarramov, N. I.</creator><creator>Bobakulov, Kh. M.</creator><creator>Turgunov, K. A.</creator><creator>Tashkhodzhaev, B.</creator><general>Springer US</general><general>Springer</general><general>Springer Nature B.V</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>ISR</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20221101</creationdate><title>Intramolecular Cyclization During Bromination of the Quinoline Alkaloid Haplophyllidine</title><author>Ubaidullaev, A. U. ; Vinogradova, V. I. ; Zhurakulov, Sh. N. ; Mukarramov, N. I. ; Bobakulov, Kh. M. ; Turgunov, K. A. ; Tashkhodzhaev, B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c575t-8c5b9e92c02bc8f20217bd9ae309cf2b00ea9e6f55580198e4fcd6ede22b9ec33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Alkaloids</topic><topic>Bromination</topic><topic>Bromine</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Crystal structure</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic Chemistry</topic><topic>Plant Sciences</topic><topic>Quinoline</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ubaidullaev, A. U.</creatorcontrib><creatorcontrib>Vinogradova, V. I.</creatorcontrib><creatorcontrib>Zhurakulov, Sh. N.</creatorcontrib><creatorcontrib>Mukarramov, N. I.</creatorcontrib><creatorcontrib>Bobakulov, Kh. M.</creatorcontrib><creatorcontrib>Turgunov, K. A.</creatorcontrib><creatorcontrib>Tashkhodzhaev, B.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Gale In Context: Science</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemistry of natural compounds</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ubaidullaev, A. U.</au><au>Vinogradova, V. I.</au><au>Zhurakulov, Sh. N.</au><au>Mukarramov, N. I.</au><au>Bobakulov, Kh. M.</au><au>Turgunov, K. A.</au><au>Tashkhodzhaev, B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Intramolecular Cyclization During Bromination of the Quinoline Alkaloid Haplophyllidine</atitle><jtitle>Chemistry of natural compounds</jtitle><stitle>Chem Nat Compd</stitle><addtitle>Chem Nat Compd</addtitle><date>2022-11-01</date><risdate>2022</risdate><volume>58</volume><issue>6</issue><spage>1101</spage><epage>1107</epage><pages>1101-1107</pages><issn>0009-3130</issn><eissn>1573-8388</eissn><abstract>Bromination of the furanoquinoline alkaloid haplophyllidine by molecular bromine and
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-bromosuccinimide was accompanied by intramolecular cyclization to form mixtures of new compounds containing additional penta-, hexa-, and spirocyclic rings incorporating the prenyl group of haplophyllidine. The structures and absolute configurations of the chiral centers of all four bromo-derivatives were elucidated using a combination of NMR spectroscopic methods and X-ray crystal structure analyses.</abstract><cop>New York</cop><pub>Springer US</pub><pmid>36406158</pmid><doi>10.1007/s10600-022-03877-6</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| source | Springer Nature - Complete Springer Journals |
| subjects | Alkaloids Bromination Bromine Chemistry Chemistry and Materials Science Chemistry/Food Science Crystal structure NMR Nuclear magnetic resonance Organic Chemistry Plant Sciences Quinoline |
| title | Intramolecular Cyclization During Bromination of the Quinoline Alkaloid Haplophyllidine |
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