Synthesis of Natural Products with Polycyclic Systems
Herein we present our unique strategies to synthesize natural products. To prepare mersicarpine, an atypical indole alkaloid, our procedure features an Eschenmoser-Tanabe fragmentation to synthesize an alkyne unit, a combination of a Sonogashira coupling and a gold(III) catalyzed cyclization to cons...
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Veröffentlicht in: | Chemical & pharmaceutical bulletin 2013/03/01, Vol.61(3), pp.251-257 |
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description | Herein we present our unique strategies to synthesize natural products. To prepare mersicarpine, an atypical indole alkaloid, our procedure features an Eschenmoser-Tanabe fragmentation to synthesize an alkyne unit, a combination of a Sonogashira coupling and a gold(III) catalyzed cyclization to construct the indole skeleton, and a one-pot process to arrange the cyclic imine and the hemiaminal moieties. Additionally, we synthesized a frog poison, histrionicotoxin, via a chirality transfer from an allenylsilane to prepare a pseudosymmetrical dienyne, dienyne metathesis to produce an optically active bicyclo [5.4.0] system, and an asymmetric propargylation. To synthesize lyconadin A, a Lycopodium alkaloid, a combination of an aza-Prins reaction and electrocyclic ring opening constructed the highly fused tetracyclic compound. The synthesis of isoschizogamine features a facile construction of the carbon framework through a Wagner-Meerwein rearrangement, a tandem metathesis, a stereoselective rhodium-mediated 1,4-addition of an arylboronic acid, and a ring-closing metathesis via a hemiaminal ether. |
doi_str_mv | 10.1248/cpb.c12-01031 |
format | Article |
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The synthesis of isoschizogamine features a facile construction of the carbon framework through a Wagner-Meerwein rearrangement, a tandem metathesis, a stereoselective rhodium-mediated 1,4-addition of an arylboronic acid, and a ring-closing metathesis via a hemiaminal ether.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.c12-01031</identifier><identifier>PMID: 23449194</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>alkaloid ; Alkaloids - chemical synthesis ; Alkaloids - chemistry ; Amphibian Venoms - chemical synthesis ; Amphibian Venoms - chemistry ; Animals ; Biological Products - chemical synthesis ; Biological Products - chemistry ; Indole Alkaloids - chemical synthesis ; Indole Alkaloids - chemistry ; Indoles - chemical synthesis ; Indoles - chemistry ; natural product ; Polycyclic Compounds - chemical synthesis ; Polycyclic Compounds - chemistry ; polycyclic system ; total synthesis</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2013/03/01, Vol.61(3), pp.251-257</ispartof><rights>2013 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2013</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c486t-b21b69da4e4da95883cbe3a2429c4076293eee98857525ebfbf432d70f9148d23</citedby><cites>FETCH-LOGICAL-c486t-b21b69da4e4da95883cbe3a2429c4076293eee98857525ebfbf432d70f9148d23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1881,27923,27924</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23449194$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yokoshima, Satoshi</creatorcontrib><title>Synthesis of Natural Products with Polycyclic Systems</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. 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The synthesis of isoschizogamine features a facile construction of the carbon framework through a Wagner-Meerwein rearrangement, a tandem metathesis, a stereoselective rhodium-mediated 1,4-addition of an arylboronic acid, and a ring-closing metathesis via a hemiaminal ether.</description><subject>alkaloid</subject><subject>Alkaloids - chemical synthesis</subject><subject>Alkaloids - chemistry</subject><subject>Amphibian Venoms - chemical synthesis</subject><subject>Amphibian Venoms - chemistry</subject><subject>Animals</subject><subject>Biological Products - chemical synthesis</subject><subject>Biological Products - chemistry</subject><subject>Indole Alkaloids - chemical synthesis</subject><subject>Indole Alkaloids - chemistry</subject><subject>Indoles - chemical synthesis</subject><subject>Indoles - chemistry</subject><subject>natural product</subject><subject>Polycyclic Compounds - chemical synthesis</subject><subject>Polycyclic Compounds - chemistry</subject><subject>polycyclic system</subject><subject>total synthesis</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkEtLAzEQgIMotlaPXmXBi5etSSb7yFGKLxAtVM8hm521W_ZRkyyy_97twwpeZg7z8TF8hFwyOmVcpLdmnU0N4yFlFNgRGTMQSRhxDsdkTCmVIYcYRuTMuRWlPKIJnJIRByEkk2JMokXf-CW60gVtEbxq31ldBXPb5p3xLvgu_TKYt1VvelOVJlj0zmPtzslJoSuHF_s9IR8P9--zp_Dl7fF5dvcSGpHGPsw4y2KZa4Ei1zJKUzAZguaCSyNoEnMJiCjTNEoiHmFWZIUAnie0kEykOYcJudl517b96tB5VZfOYFXpBtvOKQZMACSMJwN6_Q9dtZ1thu8UE0lKQVC-EYY7ytjWOYuFWtuy1rZXjKpNTzX0VENPte058Fd7a5fVmB_o34ADMNsBK-f1Jx4AbX1pKtzqYqZgMw7av-tSW4UN_ACzcocI</recordid><startdate>20130301</startdate><enddate>20130301</enddate><creator>Yokoshima, Satoshi</creator><general>The Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>20130301</creationdate><title>Synthesis of Natural Products with Polycyclic Systems</title><author>Yokoshima, Satoshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c486t-b21b69da4e4da95883cbe3a2429c4076293eee98857525ebfbf432d70f9148d23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>alkaloid</topic><topic>Alkaloids - chemical synthesis</topic><topic>Alkaloids - chemistry</topic><topic>Amphibian Venoms - chemical synthesis</topic><topic>Amphibian Venoms - chemistry</topic><topic>Animals</topic><topic>Biological Products - chemical synthesis</topic><topic>Biological Products - chemistry</topic><topic>Indole Alkaloids - chemical synthesis</topic><topic>Indole Alkaloids - chemistry</topic><topic>Indoles - chemical synthesis</topic><topic>Indoles - chemistry</topic><topic>natural product</topic><topic>Polycyclic Compounds - chemical synthesis</topic><topic>Polycyclic Compounds - chemistry</topic><topic>polycyclic system</topic><topic>total synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yokoshima, Satoshi</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yokoshima, Satoshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Natural Products with Polycyclic Systems</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2013-03-01</date><risdate>2013</risdate><volume>61</volume><issue>3</issue><spage>251</spage><epage>257</epage><pages>251-257</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>Herein we present our unique strategies to synthesize natural products. To prepare mersicarpine, an atypical indole alkaloid, our procedure features an Eschenmoser-Tanabe fragmentation to synthesize an alkyne unit, a combination of a Sonogashira coupling and a gold(III) catalyzed cyclization to construct the indole skeleton, and a one-pot process to arrange the cyclic imine and the hemiaminal moieties. Additionally, we synthesized a frog poison, histrionicotoxin, via a chirality transfer from an allenylsilane to prepare a pseudosymmetrical dienyne, dienyne metathesis to produce an optically active bicyclo [5.4.0] system, and an asymmetric propargylation. 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subjects | alkaloid Alkaloids - chemical synthesis Alkaloids - chemistry Amphibian Venoms - chemical synthesis Amphibian Venoms - chemistry Animals Biological Products - chemical synthesis Biological Products - chemistry Indole Alkaloids - chemical synthesis Indole Alkaloids - chemistry Indoles - chemical synthesis Indoles - chemistry natural product Polycyclic Compounds - chemical synthesis Polycyclic Compounds - chemistry polycyclic system total synthesis |
title | Synthesis of Natural Products with Polycyclic Systems |
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