Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment.
dc.contributor.author | Geldsetzer, Jan | |
dc.contributor.author | Kalesse, Markus | |
dc.date.accessioned | 2022-05-06T13:25:39Z | |
dc.date.available | 2022-05-06T13:25:39Z | |
dc.date.issued | 2020-04-14 | |
dc.date.submitted | 2022-05-06 | |
dc.identifier.issn | 1860-5397 | |
dc.identifier.pmid | 32362944 | |
dc.identifier.doi | 10.3762/bjoc.16.64 | |
dc.identifier.uri | http://hdl.handle.net/10033/623186 | |
dc.description.abstract | The 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.iso | en | en_US |
dc.rights | Attribution 4.0 International | * |
dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | * |
dc.subject | Z-enamide | en_US |
dc.subject | cross coupling | en_US |
dc.subject | myxobacteria | en_US |
dc.subject | natural product | en_US |
dc.subject | ribolactone | en_US |
dc.title | Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment. | en_US |
dc.type | Article | en_US |
dc.identifier.journal | Beilstein journal of organic chemistry | en_US |
dc.source.volume | 16 | |
dc.source.beginpage | 670 | |
dc.source.endpage | 673 | |
refterms.dateFOA | 2022-05-06T13:25:39Z | |
dc.source.journaltitle | Beilstein journal of organic chemistry | |
dc.source.country | Germany |