Total Syntheses of Multicaulins via Oxidative Photocyclization of Stilbenes

The Wittig reaction of 3-isopropyl-4-methoxybenzaldehyde and 2,3-dimethylbenzylphosphonium bromide afforded the corresponding stilbene mixture 16. Oxidative photocyclization of stilbene 16 with iodine facilitated the first total synthesis of 7-isopropyl-6-methoxy-1,2-dimethylphenanthrene, multicauli...

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Veröffentlicht in:	Journal of natural products (Washington, D.C.) D.C.), 2014-09, Vol.77 (9), p.2134-2137
Hauptverfasser:	Seçinti, Hatice, Burmaoğlu, Serdar, Altundaş, Ramazan, Seçen, Hasan
Format:	Artikel
Sprache:	eng
Schlagworte:	Benzaldehydes - chemistry Cyclization Molecular Structure Organophosphorus Compounds - chemistry Oxidation-Reduction Phenanthrenes - chemical synthesis Phenanthrenes - chemistry Stilbenes - chemistry
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container_title	Journal of natural products (Washington, D.C.)
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creator	Seçinti, Hatice Burmaoğlu, Serdar Altundaş, Ramazan Seçen, Hasan
description	The Wittig reaction of 3-isopropyl-4-methoxybenzaldehyde and 2,3-dimethylbenzylphosphonium bromide afforded the corresponding stilbene mixture 16. Oxidative photocyclization of stilbene 16 with iodine facilitated the first total synthesis of 7-isopropyl-6-methoxy-1,2-dimethylphenanthrene, multicaulin (1). The O-demethylation of 1 with BBr3 afforded the 7-isopropyl-1,2-dimethylphenanthren-6-ol, O-demethylmulticaulin (2).
doi_str_mv	10.1021/np5001158
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Oxidative photocyclization of stilbene 16 with iodine facilitated the first total synthesis of 7-isopropyl-6-methoxy-1,2-dimethylphenanthrene, multicaulin (1). The O-demethylation of 1 with BBr3 afforded the 7-isopropyl-1,2-dimethylphenanthren-6-ol, O-demethylmulticaulin (2).</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np5001158</identifier><identifier>PMID: 25140606</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Benzaldehydes - chemistry ; Cyclization ; Molecular Structure ; Organophosphorus Compounds - chemistry ; Oxidation-Reduction ; Phenanthrenes - chemical synthesis ; Phenanthrenes - chemistry ; Stilbenes - chemistry</subject><ispartof>Journal of natural products (Washington, D.C.), 2014-09, Vol.77 (9), p.2134-2137</ispartof><rights>Copyright © 2014 American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a315t-bbb30f6a4e7e243ead3753416d0a66578abcbc09902ec865c42005fa365250c23</citedby><cites>FETCH-LOGICAL-a315t-bbb30f6a4e7e243ead3753416d0a66578abcbc09902ec865c42005fa365250c23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np5001158$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np5001158$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25140606$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Seçinti, Hatice</creatorcontrib><creatorcontrib>Burmaoğlu, Serdar</creatorcontrib><creatorcontrib>Altundaş, Ramazan</creatorcontrib><creatorcontrib>Seçen, Hasan</creatorcontrib><title>Total Syntheses of Multicaulins via Oxidative Photocyclization of Stilbenes</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. 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The O-demethylation of 1 with BBr3 afforded the 7-isopropyl-1,2-dimethylphenanthren-6-ol, O-demethylmulticaulin (2).</description><subject>Benzaldehydes - chemistry</subject><subject>Cyclization</subject><subject>Molecular Structure</subject><subject>Organophosphorus Compounds - chemistry</subject><subject>Oxidation-Reduction</subject><subject>Phenanthrenes - chemical synthesis</subject><subject>Phenanthrenes - chemistry</subject><subject>Stilbenes - chemistry</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0F9LwzAUBfAgipvTB7-A9EXQh-pN0qTdowz_4WTC5nNJ01uWkTWzSYfz09uxuSefLlx-HDiHkEsKdxQYva9XAoBSkR2RPhUMYglMHJM-UMljnsmkR868XwAAh6E4JT0maAISZJ-8zVxQNppu6jBHjz5yVfTe2mC0aq2pfbQ2Kpp8m1IFs8boY-6C0xttzU_3cPWWT4OxBdboz8lJpazHi_0dkM-nx9noJR5Pnl9HD-NYcSpCXBQFh0qqBFNkCUdV8lTwhMoSlJQizVShCw3DITDUmRQ6YQCiUlwKJkAzPiA3u9xV475a9CFfGq_RWlWja31OhZQUUs629HZHdeO8b7DKV41ZqmaTU8i32-WH7Tp7tY9tiyWWB_k3Vgeud0Bpny9c29Rdy3-CfgEI33Sb</recordid><startdate>20140926</startdate><enddate>20140926</enddate><creator>Seçinti, Hatice</creator><creator>Burmaoğlu, Serdar</creator><creator>Altundaş, Ramazan</creator><creator>Seçen, Hasan</creator><general>American Chemical Society and American Society of Pharmacognosy</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>20140926</creationdate><title>Total Syntheses of Multicaulins via Oxidative Photocyclization of Stilbenes</title><author>Seçinti, Hatice ; Burmaoğlu, Serdar ; Altundaş, Ramazan ; Seçen, Hasan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a315t-bbb30f6a4e7e243ead3753416d0a66578abcbc09902ec865c42005fa365250c23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Benzaldehydes - chemistry</topic><topic>Cyclization</topic><topic>Molecular Structure</topic><topic>Organophosphorus Compounds - chemistry</topic><topic>Oxidation-Reduction</topic><topic>Phenanthrenes - chemical synthesis</topic><topic>Phenanthrenes - chemistry</topic><topic>Stilbenes - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Seçinti, Hatice</creatorcontrib><creatorcontrib>Burmaoğlu, Serdar</creatorcontrib><creatorcontrib>Altundaş, Ramazan</creatorcontrib><creatorcontrib>Seçen, Hasan</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>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Seçinti, Hatice</au><au>Burmaoğlu, Serdar</au><au>Altundaş, Ramazan</au><au>Seçen, Hasan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Syntheses of Multicaulins via Oxidative Photocyclization of Stilbenes</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. 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subjects	Benzaldehydes - chemistry Cyclization Molecular Structure Organophosphorus Compounds - chemistry Oxidation-Reduction Phenanthrenes - chemical synthesis Phenanthrenes - chemistry Stilbenes - chemistry
title	Total Syntheses of Multicaulins via Oxidative Photocyclization of Stilbenes
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