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Total Synthesis of (-)-Anaferine: A Further Ramification in a Diversity-Oriented Approach
The piperidine ring is a widespread motif in several natural bioactive alkaloids of both vegetal and marine origin. In the last years, a diversity-oriented synthetic (DOS) approach, aimed at the generation of a library of piperidine-based derivatives, was developed in our research group, employing c...
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| Published in: | Molecules (Basel, Switzerland) Switzerland), 2020-02, Vol.25 (5), p.1057 |
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| Main Authors: | , , , |
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| container_issue | 5 |
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| container_title | Molecules (Basel, Switzerland) |
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| creator | Bonandi, Elisa Tedesco, Giada Perdicchia, Dario Passarella, Daniele |
| description | The piperidine ring is a widespread motif in several natural bioactive alkaloids of both vegetal and marine origin. In the last years, a diversity-oriented synthetic (DOS) approach, aimed at the generation of a library of piperidine-based derivatives, was developed in our research group, employing commercially available 2-piperidine ethanol as a versatile precursor. Here, we report the exploration of another ramification of our DOS approach, that led us to the stereoselective total synthesis of (-)-anaferine, a bis-piperidine alkaloid present in
extract. This natural product was obtained in 9% overall yield over 13 steps, starting from a key homoallylic alcohol previously synthesised in our laboratory. Therefore, the collection of piperidine-derivatives accessible from 2-piperidine ethanol was enriched with a new, diverse scaffold. |
| doi_str_mv | 10.3390/molecules25051057 |
| format | article |
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extract. This natural product was obtained in 9% overall yield over 13 steps, starting from a key homoallylic alcohol previously synthesised in our laboratory. Therefore, the collection of piperidine-derivatives accessible from 2-piperidine ethanol was enriched with a new, diverse scaffold.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules25051057</identifier><identifier>PMID: 32120931</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>2-piperidine ethanol ; Alcohol ; Alkaloids ; Alkaloids - chemical synthesis ; Alkaloids - chemistry ; anaferine ; bis-piperidine alkaloids ; Cytotoxicity ; diversity-oriented synthesis ; Ethanol ; Ethanol - chemistry ; Laboratories ; Libraries ; Microorganisms ; Natural products ; Nitrogen ; Piperidine ; Piperidines - chemistry ; Plant Extracts - chemistry ; Stereoisomerism ; Stereoselectivity ; Withania - chemistry</subject><ispartof>Molecules (Basel, Switzerland), 2020-02, Vol.25 (5), p.1057</ispartof><rights>2020. This work is licensed under http://creativecommons.org/licenses/by/3.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2020 by the authors. 2020</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c493t-9a1614426065f72030b6f94a20580e73f5fdd77b81e5f15fbbcc7e988a887d13</citedby><cites>FETCH-LOGICAL-c493t-9a1614426065f72030b6f94a20580e73f5fdd77b81e5f15fbbcc7e988a887d13</cites><orcidid>0000-0001-6180-9581</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/2370222053/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/2370222053?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,25753,27924,27925,37012,37013,44590,53791,53793,75126</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32120931$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bonandi, Elisa</creatorcontrib><creatorcontrib>Tedesco, Giada</creatorcontrib><creatorcontrib>Perdicchia, Dario</creatorcontrib><creatorcontrib>Passarella, Daniele</creatorcontrib><title>Total Synthesis of (-)-Anaferine: A Further Ramification in a Diversity-Oriented Approach</title><title>Molecules (Basel, Switzerland)</title><addtitle>Molecules</addtitle><description>The piperidine ring is a widespread motif in several natural bioactive alkaloids of both vegetal and marine origin. In the last years, a diversity-oriented synthetic (DOS) approach, aimed at the generation of a library of piperidine-based derivatives, was developed in our research group, employing commercially available 2-piperidine ethanol as a versatile precursor. Here, we report the exploration of another ramification of our DOS approach, that led us to the stereoselective total synthesis of (-)-anaferine, a bis-piperidine alkaloid present in
extract. This natural product was obtained in 9% overall yield over 13 steps, starting from a key homoallylic alcohol previously synthesised in our laboratory. Therefore, the collection of piperidine-derivatives accessible from 2-piperidine ethanol was enriched with a new, diverse scaffold.</description><subject>2-piperidine ethanol</subject><subject>Alcohol</subject><subject>Alkaloids</subject><subject>Alkaloids - chemical synthesis</subject><subject>Alkaloids - chemistry</subject><subject>anaferine</subject><subject>bis-piperidine alkaloids</subject><subject>Cytotoxicity</subject><subject>diversity-oriented synthesis</subject><subject>Ethanol</subject><subject>Ethanol - chemistry</subject><subject>Laboratories</subject><subject>Libraries</subject><subject>Microorganisms</subject><subject>Natural products</subject><subject>Nitrogen</subject><subject>Piperidine</subject><subject>Piperidines - chemistry</subject><subject>Plant Extracts - chemistry</subject><subject>Stereoisomerism</subject><subject>Stereoselectivity</subject><subject>Withania - chemistry</subject><issn>1420-3049</issn><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNplkk1r3DAQhk1paT7aH9BLEfSSHNzM6MOyewgsadMGAoF0LzkJWZayWmxrK9mB_fdVsklI2pOE5n0f5h1NUXxC-MpYAydD6K2Ze5uoAIEg5JtiHzmFkgFv3r647xUHKa0BKHIU74s9RpFCw3C_uFmGSffk93acVjb5RIIjR-VxuRi1s9GP9htZkPM55mok13rwzhs9-TASPxJNvvs7G5OftuVV9HacbEcWm00M2qw-FO-c7pP9-HgeFsvzH8uzX-Xl1c-Ls8VlaXjDprLRWCHntIJKOEmBQVu5hmsKogYrmROu66Rsa7TCoXBta4y0TV3rupYdssPiYoftgl6rTfSDjlsVtFcPDyHeKh0nb3qrdCtb3UJdY6c5Zj9UDqFqLXQNCm4y63TH2sztYDuTA0Xdv4K-rox-pW7DnZIoG2QsA44eATH8mW2a1OCTsX2vRxvmpCiTIHJQXmfpl3-k6zDHMU_qQUVpHsA9EHcqE0NK0brnZhDU_Q6o_3Ygez6_TPHsePp09hdZz64U</recordid><startdate>20200227</startdate><enddate>20200227</enddate><creator>Bonandi, Elisa</creator><creator>Tedesco, Giada</creator><creator>Perdicchia, Dario</creator><creator>Passarella, Daniele</creator><general>MDPI AG</general><general>MDPI</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>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0001-6180-9581</orcidid></search><sort><creationdate>20200227</creationdate><title>Total Synthesis of (-)-Anaferine: A Further Ramification in a Diversity-Oriented Approach</title><author>Bonandi, Elisa ; Tedesco, Giada ; Perdicchia, Dario ; Passarella, Daniele</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c493t-9a1614426065f72030b6f94a20580e73f5fdd77b81e5f15fbbcc7e988a887d13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>2-piperidine ethanol</topic><topic>Alcohol</topic><topic>Alkaloids</topic><topic>Alkaloids - chemical synthesis</topic><topic>Alkaloids - chemistry</topic><topic>anaferine</topic><topic>bis-piperidine alkaloids</topic><topic>Cytotoxicity</topic><topic>diversity-oriented synthesis</topic><topic>Ethanol</topic><topic>Ethanol - chemistry</topic><topic>Laboratories</topic><topic>Libraries</topic><topic>Microorganisms</topic><topic>Natural products</topic><topic>Nitrogen</topic><topic>Piperidine</topic><topic>Piperidines - chemistry</topic><topic>Plant Extracts - chemistry</topic><topic>Stereoisomerism</topic><topic>Stereoselectivity</topic><topic>Withania - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bonandi, Elisa</creatorcontrib><creatorcontrib>Tedesco, Giada</creatorcontrib><creatorcontrib>Perdicchia, Dario</creatorcontrib><creatorcontrib>Passarella, Daniele</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>ProQuest - Health & Medical Complete保健、医学与药学数据库</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>AUTh Library subscriptions: ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>PML(ProQuest Medical Library)</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bonandi, Elisa</au><au>Tedesco, Giada</au><au>Perdicchia, Dario</au><au>Passarella, Daniele</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis of (-)-Anaferine: A Further Ramification in a Diversity-Oriented Approach</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><addtitle>Molecules</addtitle><date>2020-02-27</date><risdate>2020</risdate><volume>25</volume><issue>5</issue><spage>1057</spage><pages>1057-</pages><issn>1420-3049</issn><eissn>1420-3049</eissn><abstract>The piperidine ring is a widespread motif in several natural bioactive alkaloids of both vegetal and marine origin. 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| ispartof | Molecules (Basel, Switzerland), 2020-02, Vol.25 (5), p.1057 |
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| subjects | 2-piperidine ethanol Alcohol Alkaloids Alkaloids - chemical synthesis Alkaloids - chemistry anaferine bis-piperidine alkaloids Cytotoxicity diversity-oriented synthesis Ethanol Ethanol - chemistry Laboratories Libraries Microorganisms Natural products Nitrogen Piperidine Piperidines - chemistry Plant Extracts - chemistry Stereoisomerism Stereoselectivity Withania - chemistry |
| title | Total Synthesis of (-)-Anaferine: A Further Ramification in a Diversity-Oriented Approach |
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