Total synthesis of marine natural products separacenes A and B

A short and convergent route for the stereoselective total synthesis of separacenes A and B has been developed using (+)-methyl d-lactate and d-(-)-tartaric acid as the chiral pools. The characteristic features of this synthesis include the Trost-Rychnovsky alkyne rearrangement to construct the C -C...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic & biomolecular chemistry 2017, Vol.15 (22), p.4842-4850
Hauptverfasser: Das, Subhendu, Goswami, Rajib Kumar
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 4850
container_issue 22
container_start_page 4842
container_title Organic & biomolecular chemistry
container_volume 15
creator Das, Subhendu
Goswami, Rajib Kumar
description A short and convergent route for the stereoselective total synthesis of separacenes A and B has been developed using (+)-methyl d-lactate and d-(-)-tartaric acid as the chiral pools. The characteristic features of this synthesis include the Trost-Rychnovsky alkyne rearrangement to construct the C -C conjugated diene, the Horner-Wadsworth-Emmons olefination to form the C -C and C -C olefins and the Corey-Bakshi-Shibata reaction to install the C-13 hydroxy functionality.
doi_str_mv 10.1039/c7ob00345e
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1911619047</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1911619047</sourcerecordid><originalsourceid>FETCH-LOGICAL-c386t-19937fee0bac63ca0f1455e0ebf00699593811d4c49ba9d9c1b58130611de0d3</originalsourceid><addsrcrecordid>eNqNkE1Lw0AQhhdRbK1e_AGyRxGiM92v7EVoS_2AQi-9h81mgpE0qdnk0H_vamvPnmaYeXiZeRi7RXhEEPbJmzYHEFLRGRujNCYBJez5qZ_CiF2F8AmA1mh5yUbTVAlppzBmz5u2dzUP-6b_oFAF3pZ867qqId64fujibte1xeD7wAPtXOc8NRT4jLum4PNrdlG6OtDNsU7Y5mW5Wbwlq_Xr-2K2SrxIdZ-gtcKURJA7r4V3UKJUioDyEkBbq6xIEQvppc2dLazHXKUoQMchQSEm7P4QG2_5Gij02bYKnuraNdQOIUOLqNGCNP9AAaMEJXVEHw6o79oQOiqzXVfF5_cZQvZjNluY9fzX7DLCd8fcId9ScUL_VIpv_Btx1w</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1901764546</pqid></control><display><type>article</type><title>Total synthesis of marine natural products separacenes A and B</title><source>MEDLINE</source><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Das, Subhendu ; Goswami, Rajib Kumar</creator><creatorcontrib>Das, Subhendu ; Goswami, Rajib Kumar</creatorcontrib><description>A short and convergent route for the stereoselective total synthesis of separacenes A and B has been developed using (+)-methyl d-lactate and d-(-)-tartaric acid as the chiral pools. The characteristic features of this synthesis include the Trost-Rychnovsky alkyne rearrangement to construct the C -C conjugated diene, the Horner-Wadsworth-Emmons olefination to form the C -C and C -C olefins and the Corey-Bakshi-Shibata reaction to install the C-13 hydroxy functionality.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c7ob00345e</identifier><identifier>PMID: 28534920</identifier><language>eng</language><publisher>England</publisher><subject>Biological Products - chemical synthesis ; Biological Products - chemistry ; Molecular Structure ; Polyenes - chemical synthesis ; Polyenes - chemistry ; Stereoisomerism</subject><ispartof>Organic &amp; biomolecular chemistry, 2017, Vol.15 (22), p.4842-4850</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c386t-19937fee0bac63ca0f1455e0ebf00699593811d4c49ba9d9c1b58130611de0d3</citedby><cites>FETCH-LOGICAL-c386t-19937fee0bac63ca0f1455e0ebf00699593811d4c49ba9d9c1b58130611de0d3</cites><orcidid>0000-0001-7486-0618</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,4010,27900,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28534920$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Das, Subhendu</creatorcontrib><creatorcontrib>Goswami, Rajib Kumar</creatorcontrib><title>Total synthesis of marine natural products separacenes A and B</title><title>Organic &amp; biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>A short and convergent route for the stereoselective total synthesis of separacenes A and B has been developed using (+)-methyl d-lactate and d-(-)-tartaric acid as the chiral pools. The characteristic features of this synthesis include the Trost-Rychnovsky alkyne rearrangement to construct the C -C conjugated diene, the Horner-Wadsworth-Emmons olefination to form the C -C and C -C olefins and the Corey-Bakshi-Shibata reaction to install the C-13 hydroxy functionality.</description><subject>Biological Products - chemical synthesis</subject><subject>Biological Products - chemistry</subject><subject>Molecular Structure</subject><subject>Polyenes - chemical synthesis</subject><subject>Polyenes - chemistry</subject><subject>Stereoisomerism</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkE1Lw0AQhhdRbK1e_AGyRxGiM92v7EVoS_2AQi-9h81mgpE0qdnk0H_vamvPnmaYeXiZeRi7RXhEEPbJmzYHEFLRGRujNCYBJez5qZ_CiF2F8AmA1mh5yUbTVAlppzBmz5u2dzUP-6b_oFAF3pZ867qqId64fujibte1xeD7wAPtXOc8NRT4jLum4PNrdlG6OtDNsU7Y5mW5Wbwlq_Xr-2K2SrxIdZ-gtcKURJA7r4V3UKJUioDyEkBbq6xIEQvppc2dLazHXKUoQMchQSEm7P4QG2_5Gij02bYKnuraNdQOIUOLqNGCNP9AAaMEJXVEHw6o79oQOiqzXVfF5_cZQvZjNluY9fzX7DLCd8fcId9ScUL_VIpv_Btx1w</recordid><startdate>2017</startdate><enddate>2017</enddate><creator>Das, Subhendu</creator><creator>Goswami, Rajib Kumar</creator><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><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0001-7486-0618</orcidid></search><sort><creationdate>2017</creationdate><title>Total synthesis of marine natural products separacenes A and B</title><author>Das, Subhendu ; Goswami, Rajib Kumar</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c386t-19937fee0bac63ca0f1455e0ebf00699593811d4c49ba9d9c1b58130611de0d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Biological Products - chemical synthesis</topic><topic>Biological Products - chemistry</topic><topic>Molecular Structure</topic><topic>Polyenes - chemical synthesis</topic><topic>Polyenes - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Das, Subhendu</creatorcontrib><creatorcontrib>Goswami, Rajib Kumar</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><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Organic &amp; biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Das, Subhendu</au><au>Goswami, Rajib Kumar</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total synthesis of marine natural products separacenes A and B</atitle><jtitle>Organic &amp; biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2017</date><risdate>2017</risdate><volume>15</volume><issue>22</issue><spage>4842</spage><epage>4850</epage><pages>4842-4850</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>A short and convergent route for the stereoselective total synthesis of separacenes A and B has been developed using (+)-methyl d-lactate and d-(-)-tartaric acid as the chiral pools. The characteristic features of this synthesis include the Trost-Rychnovsky alkyne rearrangement to construct the C -C conjugated diene, the Horner-Wadsworth-Emmons olefination to form the C -C and C -C olefins and the Corey-Bakshi-Shibata reaction to install the C-13 hydroxy functionality.</abstract><cop>England</cop><pmid>28534920</pmid><doi>10.1039/c7ob00345e</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0001-7486-0618</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1477-0520
ispartof Organic & biomolecular chemistry, 2017, Vol.15 (22), p.4842-4850
issn 1477-0520
1477-0539
language eng
recordid cdi_proquest_miscellaneous_1911619047
source MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Biological Products - chemical synthesis
Biological Products - chemistry
Molecular Structure
Polyenes - chemical synthesis
Polyenes - chemistry
Stereoisomerism
title Total synthesis of marine natural products separacenes A and B
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-03T13%3A51%3A38IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Total%20synthesis%20of%20marine%20natural%20products%20separacenes%20A%20and%20B&rft.jtitle=Organic%20&%20biomolecular%20chemistry&rft.au=Das,%20Subhendu&rft.date=2017&rft.volume=15&rft.issue=22&rft.spage=4842&rft.epage=4850&rft.pages=4842-4850&rft.issn=1477-0520&rft.eissn=1477-0539&rft_id=info:doi/10.1039/c7ob00345e&rft_dat=%3Cproquest_cross%3E1911619047%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1901764546&rft_id=info:pmid/28534920&rfr_iscdi=true