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dc.contributor.authorGeldsetzer, Jan
dc.contributor.authorKalesse, Markus
dc.date.accessioned2022-05-06T13:25:39Z
dc.date.available2022-05-06T13:25:39Z
dc.date.issued2020-04-14
dc.date.submitted2022-05-06
dc.identifier.issn1860-5397
dc.identifier.pmid32362944
dc.identifier.doi10.3762/bjoc.16.64
dc.identifier.urihttp://hdl.handle.net/10033/623186
dc.description.abstractThe stereoselective synthesis of the (Z)-enamide fragment of chondrochloren (1) is described. A Buchwald-type coupling between amide 3 and (Z)-bromide 4 was used to generate the required fragment. The employed amide 3 comprising three chiral centers was obtained through a seven-step sequence starting from ᴅ-ribonic acid-1,4-lactone. The (Z)-vinyl bromide 4 is accessible in four steps from 4-hydroxybenzaldehyde. The pivotal cross coupling between both fragments was achieved after extensive experimentation with copper(I) iodide, K2CO3 and N,N'-dimethylethane-1,2-diamine.en_US
dc.language.isoenen_US
dc.rightsAttribution 4.0 International*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.subjectZ-enamideen_US
dc.subjectcross couplingen_US
dc.subjectmyxobacteriaen_US
dc.subjectnatural producten_US
dc.subjectribolactoneen_US
dc.titleTowards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment.en_US
dc.typeArticleen_US
dc.identifier.journalBeilstein journal of organic chemistryen_US
dc.source.volume16
dc.source.beginpage670
dc.source.endpage673
refterms.dateFOA2022-05-06T13:25:39Z
dc.source.journaltitleBeilstein journal of organic chemistry
dc.source.countryGermany


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Attribution 4.0 International
Except where otherwise noted, this item's license is described as Attribution 4.0 International